6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

ABSTRACT

Disclosed are triazine derivative compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides.

RELATED APPLICATIONS

This application is a continuation of U.S. Ser. No. 13/807,590, filedDec. 28, 2012, which is the U.S. national phase, pursuant to 35 U.S.C.§371, of PCT international application PCT/JP2011/062643, filed May 26,2011, designating the United States and published on Jan. 5, 2012 as WO2012/002096 A1, which claims priority to Japanese application2010-148286, filed Jun. 29, 2010. The entire contents of theaforementioned patent applications are incorporated herein by thisreference.

TECHNICAL FIELD

The present invention relates to a novel triazine derivative or itssalt, and herbicides containing it as an effective component.

BACKGROUND ART

Triazine derivatives are known from “Collection of Czechoslovak ChemicalCommunications (1969), 34(6), 1673-83,” etc., for example. However, noherbicidal activity is described for the compounds disclosed in theseliteratures. Although various compounds are reported as triazine-basedherbicides (for example, see “The Pesticide Manual 15th Edition, 2009,published by BCPC”), they all have a 1,3,5-triazine ring. Specificexamples of the 1,3,5-triazine-based agrochemicals include2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (Simazine),2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (Atrazin),2,4-bis(ethylamino)-6-meltylthio-1,3,5-triazine (Simetryn),2,4-bis(isopropylamino)-6-methylthio-1,3,5-triazine (Prometryn), and2-(1,2-dimethylpropylamino)-4-ethylamino-6-methylthio-1,3,5-triazine(Dimethametryn). Further, as a 1,2,4-triazine-based agrochemical, thereare known 4-amino-3-methyl-6-phenyl-1,2,4-triazine-5(4H)-one(Metamitron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one(Metribuzin), etc. It is disclosed in Japanese Patent ApplicationLaid-Open (JP-A) No. 8-259546 that4-(2,4-dihalogeno-5-alkoxyphenyl)-1,2,4-triazine-3,5-dione derivativeshaving a hydrocarbon substituent group at 6-position have a herbicidalactivity. It is disclosed in JP-A No. 5-51369 that3,5-diaryl-6-amino-1,2,4-triazine derivatives have a herbicidalactivity. It is disclosed in JP-A No. 5-32641 that3-mercapto-1,2,4-triazine derivatives have a herbicidal activity.

However, it is not known from any literatures that6-acyl-1,2,4-triazine-3,5-dione derivatives represented by Formula 1below have a herbicidal activity.

CITATION LIST Patent Literature

-   PLT 1: Japanese Patent Application Laid-Open No. 8-259546-   PLT 2: Japanese Patent Application Laid-Open No. 5-51369-   PLT 3: Japanese Patent Application Laid-Open No. 5-32641

Non Patent Literature

-   NPL 1: Collection of Czechoslovak Chemical Communications (1969),    34(6), 1673-83.-   NPL 2: The Pesticide Manual 15th Edition (2009, published by BCPC)

SUMMARY OF INVENTION Technical Problem

Herbicides used for useful crops and useful plants are required to be achemical preparation which can be applied to soils or leaves and exhibita sufficient herbicidal effect with low chemical dosage. Further, asthere is an increasing need concerning safety and effect on environmentof a chemical substance, development of safer herbicides is waited for.The invention is devised to cope with such problems.

Solution to Problem

In order to achieve the object above, inventors of the inventionsynthesized many triazine compounds to study the herbicidal activity ofvarious triazine derivatives, and intensively determined the herbicidalactivity and usefulness of the compounds. As a result, it is found that,when triazine derivatives of the invention are applied to weeds or soilswherein weeds thrive, an excellent herbicidal effect is obtained for along period of time, and therefore the invention is completedaccordingly.

Thus, the present invention relates to the following (1) to (43).

(1) A triazine derivative or a salt thereof represented by followingFormula 1:

[in the formula, R¹ represents a hydrogen atom; a C₁-C₁₂ alkyl group; aC₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; aC₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; aC₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; anamino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylaminoC₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; aC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkylgroup; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; ahydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group(phenyl in the group may be substituted with one substituent groupselected from Substituent group α or 2 to 5 substituent groups that arethe same or different from each other and selected from Substituentgroup α); a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆cycloalkyloxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆alkyl group; a phenyloxy C₁-C₆ alkyl group (the phenyl in the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); a phenylthio C₁-C₆ alkyl group (thephenyl in the group may be substituted with 1 to 5 identical ordifferent substituents selected from the Substituent group α); aphenylsulfinyl C₁-C₆ alkyl group (the phenyl in the group may besubstituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); a phenylsulfonyl C₁-C₆ alkyl group (thephenyl in the group may be substituted with 1 to 5 identical ordifferent substituents selected from the Substituent group α); a C₁-C₆haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substitutedwith one or more substituents selected from the Substituent group α; aphenyl C₁-C₆ alkyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a phenyl C₂-C₆alkenyl group which may be substituted with one or more substituentsselected from the Substituent group α; a phenyl C₂-C₆ alkynyl groupwhich may be substituted with one or more substituents selected from theSubstituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; aphenoxyimino C₁-C₆ alkyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a di(C₁-C₆alkoxy)C₁-C₆ alkyl group; a (R³¹R³²N—C═O)C₁-C₆ alkyl group; a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkylgroup; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylideneaminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkylgroup; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkylgroup; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group;a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom [the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α, and when the heteroatom in the heterocyclic group is a sulfuratom, the sulfur atom may be oxidized to sulfoxide or sulfone]; a C₁-C₆alkyl group substituted with a heterocyclic group comprising 3 to 10carbon atoms and one or more identical or different heteroatoms selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom [the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α]; a C₁-C₆ alkoxy C₁-C₆ alkyl groupsubstituted with a heterocyclic group comprising 3 to 10 carbon atomsand one or more identical or different heteroatoms selected from anoxygen atom, a sulfur atom, and a nitrogen atom [the group may besubstituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α]; or a C₁-C₆ alkoxy C₁-C₆ alkyl groupsubstituted with a heterocyclic-oxy group in which the heterocyclicgroup in the heterocyclic-oxy group comprising 3 to 10 carbon atoms andone or more identical or different heteroatoms selected from an oxygenatom, a sulfur atom, and a nitrogen atom [the group may be substitutedwith 1 to 5 identical or different substituents selected from theSubstituent group α];

R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; aC₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group;a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3to 10 carbon atoms and one or more identical or different heteroatomsselected from an oxygen atom, a sulfur atom, and a nitrogen atom (thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group α); a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenyl C₁-C₆ alkyl group which may be substituted with one ormore substituents selected from the Substituent group α; a phenyl C₂-C₆alkenyl group which may be substituted with one or more substituentsselected from the Substituent group α; or a phenyl C₂-C₆ alkynyl groupwhich may be substituted with one or more substituents selected from theSubstituent group α,

Y and Z represent an oxygen atom or a sulfur atom,

“A” represents any one of the following formula A-1 to A-5,

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metalcation or an ammonium cation); an amino group; a halogen atom; a cyanogroup; an isothiocyanate group; an isocyanate group; ahydroxycarbonyloxy group; a C₁-C₆ alkoxycarbonyloxy group; abenzyloxycarbonyloxy group which may be substituted with a substituentgroup selected from Substituent group α; a C₁-C₆ alkoxy group; a C₂-C₆alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group;a cyanomethylene oxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; aC₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkylcarbonyloxy group; aC₂-C₆ alkenylcarbonyloxy group; a C₂-C₆ haloalkenylcarbonyloxy group; aC₂-C₆ alkynylcarbonyloxy group; a C₂-C₆ haloalkynylcarbonyloxy group; aC₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group; a phenyloxy group which may besubstituted with one or more substituents selected from the Substituentgroup α; a benzyloxy group which may be substituted with one or moresubstituents selected from the Substituent group α; a phenylcarbonyloxygroup which may be substituted with one or more substituents selectedfrom the Substituent group α; a benzylcarbonyloxy group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenylcarbonyl C₁-C₆ alkyloxy group which may be substitutedwith one or more substituents selected from the Substituent group α; aC₁-C₁₀ alkylsulfonlyoxy group; a C₁-C₆ haloalkylsulfonlyoxy group; aphenylsulfonyloxy group which may be substituted with one or moresubstituents selected from the Substituent group α; a benzylsulfonyloxygroup which may be substituted with one or more substituents selectedfrom the Substituent group α; a C₁-C₁₀ alkylthio group; a C₁-C₁₀alkylsulfinyl group; a C₁-C₁₀ alkylsulfonyl group; a C₁-C₆ haloalkylthiogroup; a C₁-C₆ haloalkylsulfinyl group; a C₁-C₆ haloalkylsulfonyl group;a C₂-C₆ alkenylthio group; a C₂-C₆ alkenylsulfinyl group; a C₂-C₆alkenylsulfonyl group; a C₂-C₆ alkynylthio group; a C₂-C₆alkynylsulfinyl group; a C₂-C₆ alkynylsulfonyl group; a phenylthio groupwhich may be substituted with one or more substituents selected from theSubstituent group α; a benzylthio group which may be substituted withone or more substituents selected from the Substituent group α; aphenylsulfinyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a benzylsulfinylgroup which may be substituted with one or more substituents selectedfrom the Substituent group α; a phenylsulfonyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a benzylsulfonyl group which may be substituted with one ormore substituents selected from the Substituent group α; a C₁-C₁₀alkylamino group; a di(C₁-C₁₀ alkyl)amino group; a C₁-C₆alkoxycarbonylamino group; a C₁-C₆ alkoxy group substituted with aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α); a heterocyclic group comprising 3 to 10 carbon atoms and oneor more identical or different heteroatoms selected from an oxygen atom,a sulfur atom, and a nitrogen atom (the group may be substituted with 1to 5 identical or different substituents selected from the Substituentgroup α); or a heterocyclic-oxy group in which the heterocyclic group inthe heterocyclic-oxy group comprising 3 to 10 carbon atoms and one ormore identical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α),

A₁ represents a group represented by the following formula

A₂ represents a group represented by the following formula

A₃ represents a group represented by the following formula

n represents 0, 1, or 2,

R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atomor a C₁-C₆ alkyl group, herein, R⁵ and R⁸ may be joined together to forma C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain, and may form a ringtogether with adjacent carbon atoms, and R⁵ and R³⁵ may be joinedtogether to form a C₁-C₅ alkylene chain to form a ring with adjacentcarbon atoms,

R⁷, R³³, and R⁴ each independently represent a hydrogen atom, a C₁-C₆alkyl group, a C₁-C₆ haloalkyl group, a C₂-C₆ alkenyl group, a C₂-C₆alkynyl group, or a C₁-C₆ alkoxy group,

R¹⁴, R³⁵, R¹⁶, and R¹⁷ each independently represent a hydrogen atom, aC₁-C₆ alkyl group, a C₁-C₆ alkoxy group, or a benzyl group which may besubstituted with one or more substituents selected from the Substituentgroup α,

R¹⁸ represents a hydrogen atom, a C₁-C₆ alkyl group, a C₂-C₆ alkenylgroup, a C₂-C₆ alkynyl group, a cyanomethyl group, or a benzyl group,

R²⁰ represents a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆alkynyl group, a C₃-C₆ cycloalkyl group, or a C₃-C₆ cycloalkyl C₁-C₆alkyl group,

R²¹ represents a hydrogen atom, a C₁-C₆ alkyl group, or a halogen atom,

R²³ represents a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₃-C₆cycloalkyl group, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinylgroup, a C₁-C₁₀ alkylsulfonyl group, a phenylthio group which may besubstituted with one or more substituents selected from the Substituentgroup α, a benzylthio group which may be substituted with one or moresubstituents selected from the Substituent group α, a phenylsulfinylgroup which may be substituted with one or more substituents selectedfrom the Substituent group α, a benzylsulfinyl group which may besubstituted with one or more substituents selected from the Substituentgroup α, a phenylsulfonyl group which may be substituted with one ormore substituents selected from the Substituent group α, or abenzylsulfonyl group which may be substituted with one or moresubstituents selected from the Substituent group α,

R²⁴ represents a hydrogen atom, a halogen atom, a cyano group, a C₁-C₆alkyl group, a C₃-C₆ cycloalkyl group, or a C₁-C₆ alkoxycarbonylaminogroup,

R²⁵ represents a C₁-C₆ alkoxycarbonyl group, a cyano group, or a nitrogroup,

R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkylgroup; a phenyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a benzyl group whichmay be substituted with one or more substituents selected from theSubstituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆alkylcarbonyl group; a C₁-C₁₀ alkylthio carbonyl group; a C₁-C₆alkoxycarbonyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ cycloalkyl group;a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl group; aphenylsulfonyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a benzylsulfonylgroup which may be substituted with one or more substituents selectedfrom the Substituent group α; a heterocyclic group comprising 3 to 10carbon atoms and one or more identical or different heteroatoms selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom (the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); or a C₁-C₆ alkyl group substituted with aheterocyclic group in which the heterocyclic group comprising 3 to 10carbon atoms and one or more identical or different heteroatoms selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom (the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α), herein, R³¹ and R³² may be joinedtogether to form a 5- to 6-membered ring with adjacent nitrogen atom,and the one or more carbon atoms in the ring may be substituted with asulfur atom and/or an oxygen atom.

Herein, “Substituent group α” represents a group selected from a groupconsisting of:

a halogen atom; a hydroxyl group; a C₁-C₆ alkyl group; a C₃-C₆cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkylgroup; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy group; aC₃-C₆ cycloalkyloxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxygroup; a C₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonylgroup; a C₁-C₆ haloalkylthio group; a C₁-C₆ haloalkylsulfinyl group; aC₁-C₆ haloalkylsulfonyl group; an amino group; a C₁-C₆alkylcarbonylamino group; a mono(C₁-C₆ alkyl)amino group; a di(C₁-C₆alkyl)amino group; a hydroxy C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinylC₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkylgroup; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a cyano C₁-C₆ alkylgroup; a C₁-C₆ alkoxy C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyl C₁-C₆alkyloxy group; a C₁-C₆ haloalkoxy C₁-C₆ alkoxy group; a cyano C₁-C₆alkoxy group; a C₁-C₆ acyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group;a carboxyl group; a C₁-C₆ alkoxycarbonyl group; a carbamoyl group; amono(C₁-C₆ alkyl)aminocarbonyl group; a di(C₁-C₆ alkyl)aminocarbonylgroup; a nitro group; a cyano group; a phenyl group (the phenyl in thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group β); a heterocyclic group comprising2 to 10 carbon atoms and 1 to 5 identical or different heteroatomsselected from an oxygen atom, a sulfur atom, and a nitrogen atom (thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group β); a heterocyclic oxy groupcomprising 2 to 10 carbon atoms and 1 to 5 identical or differentheteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogenatom (the group may be substituted with 1 to 5 identical or differentsubstituents selected from the Substituent group β); and a C₃-C₆alkylene group formed with two adjacent substituent groups, wherein 1 to3 carbon atoms in the alkylene group may be substituted with an atomselected from a group consisting of an oxygen atom, a sulfur atom, anitrogen atom, and a carbon atom constituting an carbonyl group; and

“Substituent group β” represents a group selected from a groupconsisting of: a halogen atom, a nitro group, a cyano group, a C₁-C₆alkyl group, a C₁-C₆ haloalkyl group, a C₁-C₆ alkoxy group, and a C₁-C₆haloalkoxy group.].

(2) The triazine derivative or the salt thereof according to (1),wherein A in Formula 1 is A-1.

(3) The triazine derivative or the salt thereof according to (1) or (2),wherein in A-1, A is [X₁], A₂ is [X₃], and A₃ is [X₉].

(4) The triazine derivative or the salt thereof according to (3),wherein R⁵ and R⁶ in [X₁] is a hydrogen atom or a C₁-C₆ alkyl group, Rand R⁹ in [X₃] is a hydrogen atom or a C₁-C₆ alkyl group, and R³⁵ andR³⁶ in [X₉] is a hydrogen atom or a C₁-C₆ alkyl group, or R⁵ and R³⁵ maybind to each other via a C₁-C₅ alkylene chain to form a ring.(5) The triazine derivative or the salt thereof according to (1),wherein A in Formula 1 is A-3.(6) The triazine derivative or the salt thereof according to (5),wherein R²⁰ in A-3 is a C₁-C₆ alkyl group, and R21 in A-3 is a hydrogenatom or a C₁-C₆ alkyl group.(7) The triazine derivative or the salt thereof according to any one of(1) to (6), wherein R⁴ in A-1 is a hydroxyl group or an O⁻M⁺ (M⁻represents an alkali metal cation or an ammonium cation).(8) The triazine derivative or the salt thereof according to any one of(1) to (7), wherein Y in Formula 1 is an oxygen atom.(9) The triazine derivative or the salt thereof according to any one of(1) to (8), wherein R¹ in Formula 1 is the group selected from the groupconsisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; aC₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinylC₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group; a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenyl C₁-C₆ alkyl group which may be substituted with one ormore substituents selected from the Substituent group α; and aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom [the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α, and when the heteroatom in the heterocyclic group is a sulfuratom, the sulfur atom may be oxidized to sulfoxide or sulfone].(10) The triazine derivative or the salt thereof according to any one of(1) to (9), wherein R² in Formula 1 is the group selected from the groupconsisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenylgroup which may be substituted with one or more substituents selectedfrom the Substituent group α; and a heterocyclic group comprising 3 to10 carbon atoms and one or more identical or different heteroatomsselected from an oxygen atom, a sulfur atom, and a nitrogen atom (thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group α).(11) The triazine derivative or the salt thereof according to (1), inwhich the groups in Formula 1 are as follows: R¹ represents a C₁-C₁₂alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₁-C₆ alkylthio C₁-C₆alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; aC₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆alkyl group; a phenyloxy C₁-C₆ alkyl group (the phenyl in the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); a phenylthio C₁-C₆ alkyl group (thephenyl in the group may be substituted with 1 to 5 identical ordifferent substituents selected from the Substituent group α); aphenylsulfinyl C₁-C₆ alkyl group (the phenyl in the group may besubstituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); a phenylsulfonyl C₁-C₆ alkyl group (thephenyl in the group may be substituted with 1 to 5 identical ordifferent substituents selected from the Substituent group α); a phenylgroup which may be substituted with one or more substituents selectedfrom the Substituent group c; a phenyl C₁-C₆ alkyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenyl C₂-C₆ alkenyl group which may be substituted with oneor more substituents selected from the Substituent group α; a phenylC₂-C₆ alkynyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a C₁-C₆ alkoxyiminoC₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkylgroup; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a NR³¹R³² group; aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α, and when the heteroatom in the heterocyclic group is a sulfuratom, the sulfur atom may be oxidized to sulfoxide or sulfone); or aC₁-C₆ alkyl group substituted with a heterocyclic group in which theheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α);

R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α); a phenyl group which may be substituted with one or moresubstituents selected from the Substituent group α; or a phenyl C₁-C₆alkyl group which may be substituted with one or more substituentsselected from the Substituent group α;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1, A-3, and A-5,

A₁ is [X₁],

A₂ is [X₃] or [X₄], and

A₃ is [X₉],

in [X₁], R⁵ and R⁶ each independently represent a hydrogen atom or aC₁-C₆ alkyl group,

in [X₃], Re and R⁹ each independently represent a hydrogen atom or aC₁-C₆ alkyl group,

in [X₉], R³⁵ and R³⁶ each independently represent a hydrogen atom or aC₂-C₆ alkyl group,

herein, R⁵ and R¹ may be joined together to form a C₂-C₅ alkylene chainor a C₂-C₅ alkenylene chain, and may form a ring together with adjacentcarbon atoms, and R⁵ and R³⁵ may be joined together to form a C₁-C₅alkylene chain to form a ring with adjacent carbon atoms,

in A-3, R² is a C₁-C₆ alkyl group,

R² is a hydrogen atom or a C₁-C₆ alkyl group,

in A-5, R² represents a hydrogen atom, a C₁-C₆ alkyl group, or a C₃-C₆cycloalkyl group, R²⁵ represents a C₁-C₆ alkoxycarbonyl group, a cyanogroup, or a nitro group,

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metalcation or an ammonium cation); or a C₁-C₁₀ alkylsulfonlyoxy group;

R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkylgroup; a phenyl group which may be substituted with one or moresubstituents selected from the Substituent group α; or a benzyl groupwhich may be substituted with one or more substituents selected from theSubstituent group α; herein, R³¹ and R32 may be joined together to forma 5- to 6-membered ring with adjacent nitrogen atom, and the one or morecarbon atoms in the ring may be substituted with a sulfur atom and/or anoxygen atom,

herein, “Substituent group α” represents a group selected from a groupconsisting of:

a halogen atom; a C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₂-C₆alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkylgroup; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₂-C₆alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₁-C₆ haloalkoxy group; aC₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkysulfonylgroup; a nitro group; a cyano group; a phenyl group (the phenyl in thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group β); a heterocyclic oxy groupcomprising 2 to 10 carbon atoms and 1 to 5 heteroatoms that areoptionally selected from an oxygen atom, a sulfur atom, and a nitrogenatom (the group may be substituted with 1 to 5 identical or differentsubstituents selected from the Substituent group β); and a C₃-C₆alkylene group formed with two adjacent substituent groups, wherein 1 to3 carbon atoms in the alkylene group may be substituted with an atomselected from a group consisting of an oxygen atom, a sulfur atom, anitrogen atom, and a carbon atom constituting an carbonyl group.

(12) The triazine derivative or the salt thereof according to (1), inwhich the groups in Formula 1 are as follows:

R¹ is a group selected from a group consisting of a C₁-C₁₂ alkyl group;a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group;a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenylgroup; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyC₁-C₆ alkyl group; a phenyl group which may be substituted with one ormore substituents selected from the Substituent group α; a phenyl C₁-C₆alkyl group which may be substituted with one or more substituentsselected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkylgroup; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonylC₁-C₆ alkyl group; a NR³¹R³² group; a heterocyclic group comprising 3 to10 carbon atoms and one or more identical or different heteroatomsselected from an oxygen atom, a sulfur atom, and a nitrogen atom (thegroup may be substituted with 1 to 5 identical or different substituentsselected from the Substituent group α, and when the heteroatom in theheterocyclic group is a sulfur atom, the sulfur atom may be oxidized tosulfoxide or sulfone); and, a C₁-C₆ alkyl group substituted with aheterocyclic group in which the heterocyclic group comprising 3 to 10carbon atoms and one or more identical or different heteroatoms selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom (the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α);

R³¹ and R³² each independently represent a group selected from a groupconsisting of a hydrogen atom; a C₁-C₆ alkyl group; and, a phenyl groupwhich may be substituted with one or more substituents selected from theSubstituent group α;

R² represents a group selected from a group consisting of a C₁-C₆ alkylgroup; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkylgroup; a C₁-C₆ haloalkyl group; a heterocyclic group comprising 3 to 10carbon atoms and one or more identical or different heteroatoms selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom (the group maybe substituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α); and, a phenyl group which may besubstituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1, A-3, and A-5,

R⁴ in A-1 represents a hydroxyl group;

O⁻M⁺ (M⁻ represents an alkali metal cation or an ammonium cation);

or a C₁-C₁₀ alkylsulfonyloxy group;

in A-1, A₁ is [X₁],

A₂ is [X₃] or [X₄], and

A₃ is [X₉],

in [X₁], R⁵ and R⁶ each independently represent a hydrogen atom or aC₁-C₆ alkyl group,

in [X₃], R¹ and R⁹ each independently represent a hydrogen atom or aC₁-C₆ alkyl group,

in [X₉], R³⁵ and R³⁶ each independently represent a hydrogen atom or aC₁-C₆ alkyl group,

herein, R⁵ and R⁸ may bind to each other via a C₂-C₅ alkylene chain or aC₂-C₅ alkenylene chain to form a ring, and R⁵ and R³⁵ may bind to eachother via a C₁-C₅ alkylene chain to form a ring,

in A-3, R²⁰ is a C₁-C₆ alkyl group,

R²¹ is a hydrogen atom or a C₁-C₆ alkyl group, and

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metalcation or an ammonium cation); or a C₁-C₁₀ alkylsulfonlyoxy group;

“Substituent group α” represents a group selected from a groupconsisting of: a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxygroup; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyanogroup; a phenyl group; and a C₃-C₆ alkylene group formed with twoadjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylenegroup may be substituted with an atom selected from a group consistingof an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atomconstituting an carbonyl group.

(13) The triazine derivative or the salt thereof according to (1), inwhich the groups in Formula 1 are as follows:

R¹ represents a group selected from a group consisting of a C₁-C₁₂ alkylgroup; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkylgroup; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆haloalkenyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkylgroup; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkylgroup; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonylC₁-C₆ alkyl group; a NR³¹R³² group; a heterocyclic group selected fromthe group consisting of pyridyl group, pyrimidinyl group, pyridazinylgroup, thienyl group, isoxazolyl group, pyrazolyl group, morpholinylgroup, thiomorpholinyl group, pyrazinyl group, piperidinyl group, andpyperazinyl group (the heterocyclic group may be substituted with 1 to 5identical or different substituents selected from the Substituent groupα, and when the heteroatom in the heterocyclic group is a sulfur atom,the sulfur atom may be oxidized to sulfoxide or sulfone); and, atetrahydrofuryl-methyl group;

R³¹ and R³² each independently represent a group selected from a groupconsisting of a hydrogen atom; a C₁-C₆ alkyl group; and a phenyl group;

R² represents a group selected from a group consisting of a C₁-C₆ alkylgroup; a C₁-C₆ haloalkyl group; a pyridyl group; and a phenyl group;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1 and A-3,

R⁴ in A-1 represents a hydroxyl group; or a C₁-C₁₀ alkylsulfonlyoxygroup,

in A-1, A₁ is [X₁], A₂ is [X₃] or [X₄], and A₃ is [X₉],

in [X₁], R⁵ and R⁶ are a hydrogen atom or a C₁-C₆ alkyl group,

in [X₃], R⁸ and R⁹ are a hydrogen atom or a C₁-C₆ alkyl group,

in [X₉], R³⁵ and R³⁶ are a hydrogen atom or a C₁-C₆ alkyl group,

herein, R⁵ and R¹ may be joined together to form a C₂-C₅ alkylene chainand to form a ring,

and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain andto form a ring,

in A-3, R²⁰ is a C₁-C₆ alkyl group, R²¹ is a hydrogen atom or a C₁-C₆alkyl group, and R⁴ represents a hydroxyl group or a C₁-C₁₀alkylsulfonlyoxy group, and

“Substituent group α” represents a group selected from a groupconsisting of: a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxygroup; a C₁-C₆ haloalkoxy group; a C₁-C₈ alkylthio group; a C₃-C₆alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyanogroup; a phenyl group; and a methylenedioxy group.

(14) An agrochemical composition comprising the triazine derivative orthe salt thereof described in any one of (1) to (13), and anagriculturally acceptable carrier.

(15) The agrochemical composition according to (14), in which theagrochemical composition further comprises a surface active agent.

(16) A herbicide comprising the triazine derivative or the salt thereofdescribed in any one of (1) to (13) as an active component

(17) The herbicide according to (16), in which the herbicide has aherbicidal activity for weeds in a field or a paddy field in whichagrohorticultural plants are cultivated.

(18) The herbicide according to (17), in which the agrohorticulturalplants are agrohorticultural plants given with resistance by a breedingmethod or a genetic recombination technique.

(19) A method of eliminating weeds in soils by applying an effectiveamount of herbicides comprising the triazine derivative or the saltthereof described in any one of (16) to (18).

(20) The method according to (19), in which the soils are a farmland.

(21) The method according to (19), in which the farmland is a field or apaddy field in which agrohorticultural plants are cultivated.

(22) A triazine derivative or a salt thereof represented by followingFormula 2:

[in the formula, B represents a hydroxyl group or a C₁-C₆ alkoxy groupand R¹, R², Y, and Z have the same definitions as those described inabove Formula 1].

(23) The triazine derivative or the salt thereof according to (22),wherein Y in Formula 2 is an oxygen atom.

(24) The triazine derivative or the salt thereof according to (22) or(23), wherein R¹ in Formula 2 represents a group selected from a groupconsisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; aC₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinylC₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group; a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a phenyl C₁-C₆ alkyl group which may be substituted with one ormore substituents selected from the Substituent group α; and aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom (the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α, and when the heteroatom in the heterocyclic group is a sulfuratom, the sulfur atom may be oxidized to sulfoxide or sulfone).(25) The triazine derivative or the salt thereof according to any one of(22) to (24), wherein R² in Formula 2 represents a group selected from agroup consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; aphenyl group which may be substituted with one or more substituentsselected from the Substituent group α; and a heterocyclic groupcomprising 3 to 10 carbon atoms and one or more identical or differentheteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogenatom (the group may be substituted with 1 to 5 identical or differentsubstituents selected from the substituent group α).(26) The triazine derivative or the salt thereof according to (22) or(23), wherein B is a hydroxyl group and R² is a C₁-C₆ alkyl group.(27) The triazine derivative or the salt thereof according to (26),wherein R¹ represents a group selected from a group consisting of aphenyl group which may be substituted with one or more substituentsselected from the Substituent group α; a phenyl C₁-C₆ alkyl group whichmay be substituted with one or more substituents selected from theSubstituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkylgroup; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylideneaminooxy C₁-C₆ alkyl group; a NR³¹R³² group; and a heterocyclic groupcomprising 3 to 10 carbon atoms and one or more identical or differentheteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogenatom [the group may be substituted with 1 to 5 identical or differentsubstituents selected from the Substituent group α, and when theheteroatom in the heterocyclic group is a sulfur atom, the sulfur atommay be oxidized to sulfoxide or sulfone].(28) The triazine derivative or the salt thereof according to (26),wherein R¹ represents a group selected from a group consisting of aphenyl group which may be substituted with one or more substituentsselected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkylgroup; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a NR³¹R³² group; and aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom [the group may be substituted with 1 to5 identical or different substituents selected from the Substituentgroup α and when the heteroatom in the heterocyclic group is a sulfuratom, the sulfur atom may be oxidized to sulfoxide or sulfone].(29) The triazine derivative or the salt thereof according to (27) or(28), wherein a heterocyclic group is 5- or 6-membered aromaticheterocyclic group having 1 to 3 nitrogen atoms as a heteroatom.(30) The triazine derivative or the salt thereof according to any one of(26) to (29), wherein R³¹ and R³² each independently represent ahydrogen atom; a C₁-C₆ alkyl group; a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; a benzyl group which may be substituted with one or moresubstituents selected from the Substituent group α; a C₁-C₆alkylcarbonyl group; a C₁-C₆ alkoxycarbonyl group; a C₁-C₆ haloalkylgroup; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group;or R^(3′) and R³² may be joined together to form a 5- to 6-membered ringwith adjacent nitrogen atom, and in such case, one or more carbon atomin the ring may be substituted with a sulfur atom and/or an oxygen atom.(31) The triazine derivative or the salt thereof according to (30),wherein R³¹ and R³² each independently represent a hydrogen atom; aC₁-C₆ alkyl group; or a phenyl group which may be substituted with oneor more substituents selected from the Substituent group α.(32) The triazine derivative or the salt thereof according to any one of(26) to (31), wherein “Substituent group α” represents a group selectedfrom a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₃-C₆cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆haloalkyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkylC₁-C₆ alkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; aC₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ haloalkylthiogroup; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkylgroup; or a C₃-C₆ alkylene group formed with two adjacent substituentgroups, wherein 1 to 3 carbon atoms in the alkylene group may besubstituted with an atom selected from a group consisting of an oxygenatom, a sulfur atom, a nitrogen atom, and a carbon atom constituting ancarbonyl group.(33) The triazine derivative or the salt thereof according to (32),wherein “Substituent group α” represents a group selected from a groupconsisting of a halogen atom; a C₁-C₆ alkyl group; a C₁-C₆ haloalkylgroup; a C₁-C₆ alkoxy group; or a C₁-C₆ alkylthio group.(34) The triazine derivative or the salt thereof according to any one of(22) to (33), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of aC₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; aC₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkylgroup; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; aC₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkylgroup; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyiminoC₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substitutedwith one or more substituents selected from the Substituent group α; aphenyl C₁-C₆ alkyl group which may be substituted with one or moresubstituents selected from the Substituent group α; and a heterocyclicgroup comprising 3 to 10 carbon atoms and one or more identical ordifferent heteroatoms selected from an oxygen atom, a sulfur atom, and anitrogen atom (the group may be substituted with 1 to 5 identical ordifferent substituents selected from the Substituent group α, and whenthe heteroatom in the heterocyclic group is a sulfur atom, the sulfuratom may be oxidized to sulfoxide or sulfone); and

R² in Formula 2 represents a group selected from a group consisting of aC₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may besubstituted with one or more substituents selected from the Substituentgroup α; and a heterocyclic group comprising 3 to 10 carbon atoms andone or more identical or different heteroatoms selected from an oxygenatom, a sulfur atom, and a nitrogen atom (the group may be substitutedwith 1 to 5 identical or different substituents selected from theSubstituent group α).

(35) The triazine derivative or the salt thereof according to any one of(22) to (34), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of aC₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; aC₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkylgroup; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; aC₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkylgroup; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyiminoC₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substitutedwith one or more substituents selected from the Substituent group α; aphenyl C₁-C₆ alkyl group which may be substituted with one or moresubstituents selected from the Substituent group α; and a heterocyclicgroup selected from the group consisting of pyridyl group, pyrimidinylgroup, pyrazinyl group, pyridazinyl group, thienyl group, thiazolylgroup, isoxazolyl group, pyrazolyl group, morpholinyl group,thiomorpholinyl group, and pyperazinyl group (the group may besubstituted with 1 to 5 identical or different substituents selectedfrom the Substituent group α, and when the heteroatom in theheterocyclic group is a sulfur atom, the sulfur atom may be oxidized tosulfoxide or sulfone);

R² is a group selected from a group consisting of a C₁-C₆ alkyl group; aC₁-C₆ haloalkyl group; and a pyridyl group; and,

“Substituent group α” represents a group selected from a groupconsisting of a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenylgroup; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxygroup; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyanogroup; a phenyl group; and a methylenedioxy group.

(36) An agrochemical composition comprising the triazine derivative orthe salt thereof described in any one of (22) to (35), and anagriculturally acceptable carrier.

(37) The agrochemical composition according to (36), in which theagrochemical composition further comprises a surface active agent.

(38) A herbicide comprising the triazine derivative or the salt thereofdescribed in any one of (22) to (35) as an active component.

(39) The herbicide according to (38), in which the herbicide has aherbicidal activity for weeds in a field or a paddy field in whichagrohorticultural plants are cultivated.

(40) The herbicide according to (39), in which the agrohorticulturalplants are agrohorticultural plants given with resistance by a breedingmethod or a genetic recombination technique.

(41) A method of eliminating weeds in soils by applying an effectiveamount of herbicides comprising the triazine derivative or the saltthereof described in any one of (22) to (35).

(42) The method according to (41), in which the soils are a farmland.

(43) The method according to (41), in which the farmland is a field or apaddy field in which agrohorticultural plants are cultivated.

Advantageous Effects of Invention

The invention provides the novel triazine derivative represented byFormula 1 or its salt which can effectively control weeds. The triazinederivative of the invention or its salt exhibits an excellent herbicidaleffect against various weeds, which cause a problem particularly in anagricultural field over a long period of time from a pre-germinationstage to a growing stage, for example, a broad-leaf weed like whitepepper, Amaranthus viridis, white goosefoot, Stellaria media, chamomile,China jute, Sida spinosa, sesbania, hogweed, red poppy, morning glory,and cocklebur, annual and perennial weeds of Cyperus microiria familyincluding coco grass, edible galingale, Kyllinga brevifolia var.leiolepis, java galingale, and Cyperus iria, and gramineous weeds likebarnyard millet, finger grass, foxtail, spear grass, Syrian sorghumnitidum, short awn, and wild oat. In addition, it can control rice paddyweeds including annual weeds like Echinochloa oryzicola, Cyperusdifformis, and Monochoria vaginalis and perennial weeds like Sagittariapygrnaea, Sagittaria trifolia, Cyperus serotinus, Elcocharis kuroguwai,Scirpus hotarui, and Alisma canaliculatum.

Further, the compound of the invention is highly safe to useful cropsand useful plants, in particular, to rice, wheat, barley, corn, grainsorghum, soybean, cotton, sugar beet, etc.

Thus, the invention provides an agrochemical composition having anexcellent effect as herbicides.

DESCRIPTION OF EMBODIMENTS

The definitions of the terms used in the present Description are givenbelow.

Halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom,or an iodine atom.

The descriptions like C₁-C₆ indicate the number of carbon atoms in asubstituent group described hereinbelow. For example, C₁-C₆ means 1 to 6carbon atoms.

The C₁-C₆ alkyl group represents, unless specified otherwise, a linearor branched alkyl group having 1 to 6 carbon atoms, and examples thereofinclude a group like methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-methylpropyl,neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and1-ethyl-2-methylpropyl.

The C₁-C₁₂ alkyl group represents, unless specified otherwise, a linearor branched alkyl group having 1 to 12 carbon atoms, and examplesthereof include, in addition to those exemplified above for the C₁-C₆alkyl group, a group like heptyl, 1-methylhexyl, 5-methylhexyl,1,1-dimethylpentyl, 2,2-dimethylpentyl, 4,4-dimethylpentyl,1-ethylpentyl, 2-ethylpentyl, 1,1,3-trimethylbutyl,1,2,2-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl,2,3,3-trimethylbutyl, 1-propylbutyl, 1,1,2,2-tetramethylpropyl, octyl,1-methylheptyl, 3-methylheptyl, 6-methylheptyl, 2-ethylhexyl,5,5-dimethylhexyl, 2,4,4-trimethylpentyl, 1-ethyl-1-methylpentyl, nonyl,1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 7-methyloctyl,1-ethylheptyl, 1,1-dimethylheptyl, 6,6-dimethylheptyl, decyl,1-methylnonyl, 2-methylnonyl, 6-methylnonyl, 1-ethyloctyl,1-propylheptyl, n-nonyl, and n-decyl.

The C₃-C₆ cycloalkyl group represents, unless specified otherwise, acycloalkyl group having 3 to 6 carbon atoms, and examples thereofinclude a group like cyclopropyl, cyclobutyl, cyclopentyl, andcyclohexyl.

The C₃-C₆ cycloalkenyl group represents, unless specified otherwise, acycloalkenyl group having 3 to 6 carbon atoms, and examples thereofinclude a group like cyclopentenyl and cyclohexenyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with acycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety andalkyl moiety have the same definitions as above, and examples thereofinclude a group like cyclopropylmethyl, 1-cyclopropylethyl,2-cyclopropylethyl, 1-cyclopropylpropyl, 2-cyclopropylpropyl,3-cyclopropylpropyl, cyclobutylmethyl, cyclopentylmethyl, andcyclohexylmethyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group represents an (alkyl)-O— group(i.e., alkoxy group) having 1 to 6 carbon atoms substituted with acycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety andalkyl moiety have the same definitions as above, and examples thereofinclude a group like cyclopropylmethoxy, 1-cyclopropylethoxy,2-cyclopropylethoxy, 1-cyclopropylpropoxy, 2-cyclopropylpropoxy,3-cyclopropylpropoxy, cyclobutylmethoxy, cyclopentylmethoxy, andcyclohexylmethoxy.

The C₃-C₆ halocycloalkyl group represents, unless specified otherwise, acycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, orpreferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety and thehalogen atom have the same definitions as above, and examples thereofinclude a group like 2,2-difluorocyclopropyl and2,2-dichlorocyclopropyl.

The C₃-C₆ halocycloalkyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with acycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, orpreferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety, thealkyl moiety, and the halogen atom have the same definitions as above,and examples thereof include a group like 2,2-difluorocyclopropylmethyland 2,2-dichlorocyclopropylmethyl.

The amino C₁-C₆ alkyl group represents, unless specified otherwise, analkyl group having 1 to 6 carbon atoms substituted with an amino group,wherein the alkyl moiety has the same definition as above, and examplesthereof include a group like 2-aminoethyl and 3-aminopropyl.

The nitro C₁-C₆ alkyl group represents, unless specified otherwise, analkyl group having 1 to 6 carbon atoms substituted with a nitro group,wherein the alkyl moiety has the same definition as above, and examplesthereof include a group like nitromethyl and 2-nitroethyl.

The C₁-C₆ haloalkyl group represents a linear or branched alkyl grouphaving 1 to 6 carbon atoms substituted with a halogen atom, and examplesthereof include a group like fluoromethyl, chloromethyl, bromomethyl,difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl,2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-difluoroethyl,1,2-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl,2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl,2-bromo-2-chloroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl,1-chloro-1,2,2,2-tetrafluoroethyl, 1-chloropropyl, 2-chloropropyl,3-chloropropyl, 2-bromopropyl, 3-bromopropyl, 2-bromo-1-methylethyl,3-iodopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl,3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,3-bromo-3,3-difluoropropyl, 3,3-dichloro-3-fluoropropyl,2,2,3,3-tetrafluoropropyl, l-bromo-3,3,3-trifluoropropyl,2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl,heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl,2,3-dichloro-1,1,2,3,3-pentafluoropropyl, 2-chlorobutyl, 3-chlorobutyl,4-chlorobutyl, 2-chloro-1,1-dimethylethyl, 4-bromobutyl,3-bromo-2-methylpropyl, 2-bromo-1,1-dimethylethyl,2,2-dichloro-1,1-dimethylethyl, 2-chloro-1-chloromethyl-2-methylethyl,4,4,4-tifluorobutyl, 3,3,3-trifluoro-1-methylpropyl,3,3,3-trifluoro-2-methylpropyl, 2,3,4-trichlorobutyl,2,2,2-trichloro-1,1-dimethylethyl, 4-chloro-4,4-difluorobutyl,4,4-dichloro-4-fluorobutyl, 4-bromo-4,4-difluorobutyl,2,4-dibromo-4,4-difluorobutyl, 3,4-dichloro-3,4,4-trifluorobutyl,3,3-dichloro-4,4,4-tifluorobutyl, 4-bromo-3,3,4,4-tetrafluorobutyl,4-bromo-3-chloro-3,4,4-tifluorobutyl, 2,2,3,3,4,4-hexafluorobutyl,2,2,3,4,4,4-hexafluorobutyl,2,2,2-trifluoro-1-methyl-1-trifluoromethylethyl,3,3,3-trifluoro-2-trifluoromethylpropyl, 2,2,3,3,4,4,4-heptafluorobutyl,2,3,3,3-tetrafluoro-2-trifluoromethylpropyl,1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl,4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 5-fluoropentyl,5-chloropentyl, 5,5-difluoropentyl, 5,5-dichloropentyl,5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl, and5,5,5,6,6,6-pentafluorohexyl.

The C₂-C₆ alkenyl group represents, unless specified otherwise, a linearor branched alkenyl group having 2 to 6 carbon atoms, and examplesthereof include a group like vinyl, 1-propenyl, isopropenyl, 2-propenyl,1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl,3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl,1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl,3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl,3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl,2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl,1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl,1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl)vinyl,1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl,1-(isopropyl)-2-propenyl, 2-methyl-2-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl,1-vinyl-3-butenyl, and 2,4-hexadienyl.

The C₂-C₆ alkynyl group represents, unless specified otherwise, a linearor branched alkynyl group having 2 to 6 carbon atoms, and examplesthereof include a group like ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl,1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl,4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl,1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl,3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl,1,1-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

The C₂-C₆ halolalkenyl group represents, unless specified otherwise, alinear or branched alkenyl group having 2 to 6 carbon atoms substitutedwith 1 to 11 halogen atoms that are the same or different from eachother, and examples thereof include 2-chlorovinyl, 2-bromovinyl,2-iodovinyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl,1-chloromethylvinyl, 2-bromo-1-methylvinyl, 1-trifluoromethylvinyl,3,3,3-trichloro-1-propenyl, 3-bromo-3,3-difluoro-1-propenyl,2,3,3,3-tetrachloro-1-propenyl, 1-trifluoromethyl-2,2-difluorovinyl,2-chloro-2-propenyl, 3,3-difluoro-2-propenyl,2,3,3-trichloro-2-propenyl, 4-bromo-3-chloro-3,4,4-trifluoro-1-butenyl,1-bromomethyl-2-propenyl, 3-chloro-2-butenyl, 4,4,4-trifluoro-2-butenyl,4-bromo-4,4-difluoro-2-butenyl, 3-bromo-3-butenyl,3,4,4-trifluoro-3-butenyl, 3,4,4-tribromo-3-butenyl,3-bromo-2-methyl-2-propenyl, 3,3-difluoro-2-methyl-2-propenyl,3,3,3-trifluoro-2-methylpropenyl, 3-chloro-4,4,4-trifluoro-2-butenyl,3,3,3-trifluoro-1-methyl-1-propenyl, 3,4,4-trifluoro-1,3-butadienyl,3,4-dibromo-1-pentenyl, 4,4-difluoro-3-methyl-3-butenyl,3,3,4,4,5,5,5-heptafluoro-1-pentenyl, 5,5-difluoro-4-pentenyl,4,5,5-trifluoro-4-pentenyl,3,4,4,4-tetrafluoro-3-trifluoromethyl-1-butenyl,4,4,4-trifluoromethyl-3-methyl-2-butenyl,3,5,5-trifluoro-2,4-pentadienyl, 4,4,5,5,6,6,6-heptafluoro-2-hexenyl,3,4,4,5,5,5-hexafluoro-3-trifluoromethyl-1-pentenyl,4,5,5,5-tetrafluoro-4-trifluoromethyl-2-pentenyl, and5-bromo-4,5,5-trifluoro-4-trifluoromethyl-2-pentenyl.

The C₂-C₆ haloalkynyl group represents, unless specified otherwise, alinear or branched alkynyl group having 2 to 6 carbon atoms substitutedwith 1 to 9 halogen atoms that are the same or different from eachother, and examples thereof include 3-chloro-2-propynyl,3-bromo-2-propynyl, 3-iodo-2-propynyl, 3-chloro-1-propynyl, and5-chloro-4-pentynyl.

The C₁-C₆ alkoxy group represents an (alkyl)-O— group having 1 to 6carbon atoms, wherein the alkyl moiety has the same definition as above,and examples thereof include a group like methoxy, ethoxy, propoxy,isopropoxy, butoxy, pentyloxy, and hexyloxy.

The C₁-C₆ haloalkoxy group represents a linear or branched alkyl-O—group having 1 to 6 carbon atoms substituted with 1 to 13 halogen atomsthat are the same or different from each other, wherein the haloalkylmoiety has the same definition as above, and examples thereof include agroup like chloromethoxy, difluoromethoxy, chlorodifluoromethoxy,trifluoromethoxy, and 2,2,2-trifluoroethoxy.

The C₁-C₆ alkoxy C₁-C₆ alkyl group represents an alkyl group having 1 to6 carbon atoms substituted with an alkoxy group having 1 to 6 carbonatoms, wherein the alkyl moiety and alkoxy moiety have the samedefinitions as above, and examples thereof include a group likemethoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl,methoxyethyl, and butoxyethyl.

The hydroxy C₁-C₆ alkyl group represents, unless specified otherwise, analkyl group having 1 to 6 carbon atoms substituted with a hydroxy group,wherein the alkyl moiety has the same definition as above, and examplesthereof include a group like 2-hydroxyethyl and 3-hydroxypropyl.

The C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group represents an alkylgroup having 1 to 6 carbon atoms substituted with an alkoxy having 1 to6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms,wherein the alkyl moiety and alkoxy moiety have the same definitions asabove, and examples thereof include a group like2-(2-methoxyethoxyl)ethyl and 2-(2-ethoxyethoxy)ethyl.

The phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with analkoxy group having 1 to 6 carbon atoms substituted with a phenyl,wherein the alkyl moiety and alkoxy moiety have the same definitions asabove, and examples thereof include a group like benzyloxymethyl andbenzyloxyethyl.

The C₁-C₆ haloalkoxy C₁-C₆ alkyl group represents an alkyl group having1 to 6 carbon atoms substituted with a haloalkoxy group having 1 to 6carbon atoms, wherein the haloalkoxy moiety and alkyl moiety have thesame definitions as above, and examples thereof include a group likechloromethoxymethyl, difluoromethoxymethyl, chlorodifluoromethoxymethyl,trifluoromethoxymethyl, and 2,2,2-trifluoroethoxymethyl.

The C₁-C₆ haloalkoxy C₁-C₆ alkoxy group represents, unless specifiedotherwise, an alkoxy group having 1 to 6 carbon atoms substituted with ahaloalkoxy group having 1 to 6 carbon atoms, wherein the haloalkoxymoiety and alkoxy moiety have the same definitions as above, andexamples thereof include a group like chloromethoxymethoxy,difluoromethoxymethoxy, chlorodifluoromethoxymethoxy,trifluoromethoxymethoxy, and 2,2,2-trifluoroethoxymethoxy.

The C₃-C₆ cycloalkyloxy group represents, unless specified otherwise, a(cycloalkyl)-O-group having 3 to 6 carbon atoms, wherein the cycloalkylmoiety has the same definition as above, and examples thereof include agroup like cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, andcyclohexyloxy.

The C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group represents an alkyl grouphaving 1 to 6 carbon atoms substituted with a (cycloalkyl)-O— grouphaving 3 to 6 carbon atoms, wherein the alkyl moiety and cycloalkylmoiety have the same definitions as above, and examples thereof includea group like cyclopropyloxymethyl, cyclobutyloxymethyl,cyclopentyloxymethyl, and cyclohexyloxymethyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with an alkoxy group having 1 to 6 carbon atoms substitutedwith a cycloalkyl group having 3 to 6 carbon atoms, wherein the alkylmoiety, alkoxy moiety, and cycloalkyl moiety have the same definitionsas above, and examples thereof include a group likecyclopropylmethyloxymethyl, cyclobutylmethyloxymethyl,cyclopentylmethyloxymethyl, and cyclohexylmethyloxymethyl.

The (R³¹R³²N—C≡O) C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with a(R³¹R³²N—OC—) group, wherein the alkyl moiety has the same definition asabove, and examples thereof include a group likeN,N-dimethylaminocarbonylmethyl, N,N-dimethylaminocarbonylethyl, andN-methyl-N-ethylaminocarbonylmethyl.

The C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with analkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxymoiety and alkyl moiety have the same definitions as above, and examplesthereof include a group like 2-methoxy-2-oxoethyl, 2-ethoxy-2-oxoethyl,and 2-tert-butoxy-2-oxoethyl.

The C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group represents, unless specifiedotherwise, an alkoxy group having 1 to 6 carbon atoms substituted withan alkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxymoiety and alkyl moiety have the same definitions as above, and examplesthereof include a group like a 2-methoxy-2-oxoethoxy group, a2-ethoxy-2-oxoethoxy group, and a 2-tert-butoxy-2-oxoethoxy group.

The C₁-C₆ alkylcarbonyl group represents an (alkyl (having 1 to 6 carbonatoms))-C(═O)-group, wherein the alkyl moiety has the same definition asabove, and examples thereof include acetyl and propionyl.

The C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with analkylcarbonyl group having 1 to 6 carbon atoms, wherein thealkylcarbonyl moiety and alkyl moiety have the same definitions asabove, and examples thereof include a group like 2-oxopropyl,3-oxopropyl, and 2-oxobutyl.

The C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with an (alkyl (having 1 to 6 carbon atoms))-C(═O)O— group,wherein the alkyl moiety has the same definition as above, and examplesthereof include a group like acetoxymethyl, propionyloxymethyl,isopropionyloxymethyl, and pivaloyloxymethyl.

The C₁-C₆ alkylidene group represents, unless specified otherwise, adivalent alkylidene group having 1 to 6 carbon atoms, wherein a singlecarbon carries a divalent charge and the alkyl moiety has the samedefinition as above, and examples thereof include a group like amethylene group, an ethylidene group, and an isopropylidene group.

The C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with (alkylidene (having 1 to 6 carbon atoms))=N—O—, whereinthe alkylidene moiety and alkyl moiety have the same definitions asabove, and examples thereof include a group likemethyleneaminooxymethyl, 2-(ethylidene aminooxy)ethyl, and2-(isopropylidene aminooxy)ethyl.

The C₂-C₆ alkenyloxy group represents, unless specified otherwise, an(alkenyl)-O— group having 2 to 6 carbon atoms, wherein the alkenylmoiety has the same definition as above, and examples thereof include agroup like 2-propenyloxy.

The C₂-C₆ alkynyloxy group represents, unless specified otherwise, an(alkynyl)-O— group having 2 to 6 carbon atoms, wherein the alkynylmoiety has the same definition as above, and examples thereof include2-propynyloxy.

The phenyloxy C₁-C₆ alkyl group represents, unless specified otherwise,an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-O—group, wherein the alkyl moiety has the same definition as above, andexamples thereof include a group like phenoxymethyl, 2-phenoxyethyl, and3-phenoxypropyl.

The phenylthio C₁-C₆ alkyl group represents, unless specified otherwise,an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-S—group, wherein the alkyl moiety has the same definition as above, andexamples thereof include a group like phenylthiomethyl,2-phenylthioethyl, and 3-phenylthiopropyl.

The phenylsulfinyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with a(phenyl)-SO— group, wherein the alkyl moiety has the same definition asabove, and examples thereof include a group like phenylsulfinylmethyl,2-phenylsulfinylethyl, and 3-phenylsulfinylpropyl.

The phenylsulfonyl C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with a(phenyl)-SO₂— group, wherein the alkyl moiety has the same definition asabove, and examples thereof include a group like 2-phenylsulfonylethyl,3-phenylsulfonylpropyl, and 4-phenylsulfonylbutyl.

The C₁-C₆ alkoxyimino group represents, unless specified otherwise, an(alkoxy)-N═ group having 1 to 6 carbon atoms, wherein the alkoxy moietyhas the same definition as above, and examples thereof includemethoxyimino and ethoxyimino.

The C₁-C₆ alkoxyimino C₁-C₆ alkyl group represents an alkyl group having1 to 6 carbon atoms substituted with an alkoxyimino group having 1 to 6carbon atoms, wherein the alkoxyimino moiety and alkyl moiety have thesame definitions as above, and examples thereof includemethoxyiminomethyl and ethoxyiminomethyl.

The phenoxyimino group represents, unless specified otherwise, a(substituted) (phenoxy)-N═ group, and examples thereof includephenoxyimino.

The phenoxyimino C₁-C₆ alkyl group represents an alkyl group having 1 to6 carbon atoms substituted with a phenoxyimino group, wherein thephenoxyimino moiety and alkyl moiety have the same definitions as above,and examples thereof include phenoxyiminomethyl.

The di(C₁-C₆ alkoxy) C₁-C₆ alkyl group represents an alkyl group having1 to 6 carbon atoms di-substituted with an alkoxy group having 1 to 6carbon atoms, and examples thereof include (2,2-dimethoxy)ethyl,(3,3-dimethoxy)propyl, (2,2-diethoxy)ethyl group, and a(3,3-diethoxy)propyl.

The formyl C₁-C₆ alkyl group represents an alkyl group having 1 to 6carbon atoms substituted with a formyl group, wherein the alkyl moietyhas the same definition as above, and examples thereof include(2-formyl)ethyl and (3-formyl)propyl.

The C₁-C₆ alkylthio group represents an (alkyl)-S— group having 1 to 6carbon atoms, wherein the alkyl moiety has the same definition as above,and examples thereof include methylthio, ethylthio, n-propylthio, andisopropylthio.

The C₁-C₁₀ alkylthio group represents an (alkyl)-S— group having 1 to 10carbon atoms, wherein the alkyl moiety has the same definition as above,and examples thereof include, in addition to those exemplified above forthe C₁-C₆ alkylthio group, n-heptylthio, n-octylthio, n-nonylthio, andn-decylthio.

The C₁-C₆ alkylsulfinyl group represents an (alkyl)-SO— group having 1to 6 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include methylsulfinyl, ethylsulfinyl,n-propylsulfinyl, and isopropylsulfinyl.

The C₁-C₁₀ alkylsulfinyl group represents an (alkyl)-S— group having 1to 10 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include, in addition to those exemplifiedabove for the C₁-C₆ alkylsulfinyl group, n-heptylsulfonyl,n-octylsulfinyl, n-nonylsulfonyl, and n-decylsulfinyl.

The C₁-C₆ alkylsulfonyl group represents an (alkyl)-SO₂— group having 1to 6 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include methylsulfonyl, ethylsulfonyl,n-propylsulfonyl, and isopropylsulfonyl.

The C₁-C₁₀ alkylsulfonyl group represents an (alkyl)-SO₂— group having 1to 10 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include, in addition to those exemplifiedabove for the C₁-C₆ alkylsulfonyl group, n-heptylsulfonyl,n-octylsulfonyl, n-nonylsulfonyl, and n-decylsulfonyl.

The C₂-C₆ alkenylthio group represents an (alkenyl)-S— group having 2 to6 carbon atoms, wherein the alkenyl moiety has the same definition asabove, and examples thereof include a group like allylthio.

The C₂-C₆ alkenylsulfinyl group represents an (alkenyl)-SO— group having3 to 6 carbon atoms, wherein the alkenyl moiety has the same definitionas above, and examples thereof include a group like allylsulfinyl.

The C₂-C₆ alkenylsulfonyl group represents an (alkenyl)-SO₂— grouphaving 2 to 6 carbon atoms, wherein the alkenyl moiety has the samedefinition as above, and examples thereof include a group likeallylsulfonyl.

The C₂-C₆ alkynylthio group represents an (alkynyl)-S— group having 2 to6 carbon atoms, wherein the alkynyl moiety has the same definition asabove, and examples thereof include a group like 2-propynylthio.

The C₂-C₆ alkynylsulfinyl group represents an (alkynyl)-SO— group having2 to 6 carbon atoms, wherein the alkynyl moiety has the same definitionas above, and examples thereof include a group like 2-propynylsulfinyl.

The C₂-C₆ alkenylsulfonyl group represents an (alkynyl)-SO₂— grouphaving 2 to 6 carbon atoms, wherein the alkynyl moiety has the samedefinition as above, and examples thereof include a group like2-propynylsulfonyl.

The C₁-C₁₀ alkylsulfonyloxy group represents an (alkyl)SO₂—O— grouphaving 1 to 10 carbon atoms, wherein the alkyl moiety has the samedefinition as above, and examples thereof include methylsulfonyloxy andethylsulfonyloxy.

The C₁-C₆ alkylthio C₁-C₆ alkyl group represents an alkyl group having 1to 6 carbon atoms substituted with an alkylthio group having 1 to 6carbon atoms, wherein the alkyl moiety and alkylthio moiety have thesame definitions as above, and examples thereof include methylthiomethyland ethylthiomethyl.

The C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group represents an alkyl grouphaving 1 to 6 carbon atoms substituted with an alkylsulfinyl grouphaving 1 to 6 carbon atoms, wherein the alkyl moiety and alkylsulfinylmoiety have the same definitions as above, and examples thereof includemethylsulfinylmethyl and ethylsulfinylmethyl.

The C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group represents an alkyl grouphaving 1 to 6 carbon atoms substituted with an alkylsulfonyl grouphaving 1 to 6 carbon atoms, wherein the alkyl moiety and alkylsulfonylmoiety have the same definitions as above, and examples thereof includemethylsulfonylmethyl and ethylsulfonylmethyl.

The C₁-C₆ alkoxy C₁-C₆ alkoxy group represents an alkoxy group having 1to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms,wherein the alkoxy moiety has the same definition as above, and examplesthereof include a group like methoxymethoxy, ethoxymethoxy,2-methoxyethoxy, and 2-ethoxyethoxy.

The C₁-C₆ haloalkylthio C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with a(haloalkyl)-S— group having 1 to 6 carbon atoms, wherein the alkylmoiety and haloalkyl moiety have the same definitions as above, andexamples thereof include a group like difluoromethylthiomethyl andtrifluoromethylthiomethyl.

The C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with a (haloalkyl)-SO— group having 1 to 6 carbon atoms,wherein the alkyl moiety and haloalkyl moiety have the same definitionsas above, and examples thereof include a group likedifluoromethylsulfinylmethyl and trifluoromethylsulfinylmethyl.

The C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with a (haloalkyl)-SO₂— group having 1 to 6 carbon atoms,wherein the alkyl moiety and haloalkyl moiety have the same definitionsas above, and examples thereof include a group likedifluoromethylsulfonylmethyl and trifluoromethylsulfonylmethyl.

The C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unlessspecified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with an alkoxy group having 1 to 6 carbon atoms substitutedwith an alkylthio group having 1 to 6 carbon atoms, wherein thealkylthio moiety, alkoxy moiety, and alkyl moiety have the samedefinitions as above, and examples thereof include a group like2-methylthioethoxymethyl and 2-ethylthioethoxymethyl.

The C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents,unless specified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with an alkoxy group having 1 to 6 carbon atoms substitutedwith an alkynylsulfinyl group having 1 to 6 carbon atoms, wherein thealkynylsulfinyl moiety, alkoxy moiety, and alkyl moiety have the samedefinitions as above, and examples thereof include a group like2-methylsulfinyl ethoxymethyl and 2-ethylsulfinyl ethoxymethyl.

The C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents,unless specified otherwise, an alkyl group having 1 to 6 carbon atomssubstituted with an alkoxy group having 1 to 6 carbon atoms substitutedwith an alkynylsulfonyl group having 1 to 6 carbon atoms, wherein thealkylsulfonyl moiety, alkoxy moiety, and alkyl moiety have the samedefinitions as above, and examples thereof include a group like2-methylsulfonylethoxymethyl and 2-ethylsulfonylethoxymethyl.

The C₁-C₆ acyl group represents an acyl group derived from C₁-C₆carboxylic acid, and examples thereof include an acetyl group and apropionyl group.

The C₁-C₆ alkylcarbonyl group represents an (alkyl (having 1 to 6 carbonatoms))-C(═O)— group, wherein the alkyl moiety has the same definitionas above, and examples thereof include an acetyl group and a propionylgroup.

The C₁-C₆ alkylcarbonyloxy group represents an (alkyl (having 1 to 6carbon atoms))-C(═O)—O— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include acetoxy andpropionyloxy.

The C₁-C₆ haloalkylcarbonyloxy group represents a (haloalkyl (having 1to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkyl moiety has thesame definition as above, and examples thereof include a group likechloromethylcarbonyloxy, difluoromethylcarbonyloxy,chlorodifluoromethylcarbonyloxy, trifluoromethylcarbonyloxy, and2,2,2-trifluoroethylcarbonyloxy.

The C₂-C₆ alkenylcarbonyloxy group represents an (alkenyl (having 2 to 6carbon atoms))-C(═O)—O— group, wherein the alkenyl moiety has the samedefinition as above, and examples thereof include a group like1-propenylcarbonyloxy, 2-propenylcarbonyloxy, 1-butenylcarbonyloxy, and1-methyl-1-propenylcarbonyloxy.

The C₂-C₆ halolalkenylcarbonyloxy group represents a (haloalkenyl(having 2 to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkenylmoiety has the same definition as above, and examples thereof include agroup like 3-chloro-2-propenylcarbonyloxy and3-bromo-2-propenylcarbonyloxy.

The C₂-C₆ alkynylcarbonyloxy group represents an (alkynyl (having 2 to 6carbon atoms))-C(═O)—O— group, wherein the alkynyl moiety has the samedefinition as above, and examples thereof include a group like1-propynylcarbonyloxy and 2-propynylcarbonyloxy.

The C₂-C₆ haloalkynylcarbonyloxy group represents a (haloalkynyl (having2 to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkynyl moiety hasthe same definition as above, and examples thereof include a group like3-chloro-1-propynylcarbonyloxy and3,3,3-trifluoro-1-propynylcarbonyloxy.

The C₂-C₆ alkylidene amino group represents an alkyl (having 1 to 5carbon atoms)-CH≡N-group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include a group likeethylideneamino and propylideneamino.

The di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group represents anamino group substituted with an alkylidene group having 1 to 6 carbonatoms substituted with an amino group di-substituted with an alkyl grouphaving 1 to 10 carbon atoms, wherein the alkyl moiety has the samedefinition as above, and examples thereof include a group like adimethylamino methylidene amino group and a diethylamino methylideneamino group.

The C₁-C₁₀ alkylamino group represents an (alkyl)-NH— group having 1 to10 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include methylamino and ethylamino.

The di(C₁-C₁₀ alkyl)amino group represents an (alkyl)₂N— group, whereinthe alkyl moiety has the same definition as above, and examples thereofinclude dimethylamino, diethylamino, methylethylamino, dipropylamino,and dibutylamino.

The mono(C₁-C₆ alkyl)amino group represents an (alkyl)-NH— group having1 to 6 carbon atoms, wherein the alkyl moiety has the same definition asabove, and examples thereof include a group like methylamino andethylamino.

The di(C₁-C₆ alkyl)amino group represents an (alkyl (having 1 to 6carbon atoms))₂N— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include a group likedimethylamino, diethylamino, methylethylamino, dipropylamino, anddibutylamino.

The C₁-C₆ alkylamino C₁-C₆ alkyl group represents an alkyl group having1 to 6 carbon atoms substituted with an alkylamino group having 1 to 6carbon atoms, wherein the alkyl moiety has the same definition as above,and examples thereof include N-methylaminomethyl and N-methylaminoethyl.

The di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group represents an alkyl grouphaving 1 to 6 carbon atoms substituted with an (alkyl (having 1 to 6carbon atoms))₂N— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof includeN,N-dimethylaminomethyl and N,N-dimethylaminoethyl.

The C₁-C₆ alkoxycarbonyl amino group represents an amino groupsubstituted with an (alkoxy (having 1 to 6 carbon atoms))-C(═O)— group,wherein the alkoxy moiety has the same definition as above, and examplesthereof include methoxycarbonyl amino and ethoxycarbonyl amino.

The C₁-C₆ alkylcarbonyl amino group represents, unless specifiedotherwise, an amino group substituted with an alkylacarbonyl grouphaving 1 to 6 carbon atoms, wherein the alkylcarbonyl moiety has thesame definition as above, and examples thereof include a group likeformamide, acetamide, and propionamide.

The C₁-C₆ alkoxycarbonyl group represents an (alkyl (having 1 to 6carbon atoms))-O—C(═O)— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include methoxycarbonyl,ethoxycarbonyl, n-propoxycarbonyl, and isopropoxycarbonyl.

The C₁-C₁₀ alkylthiocarbonyl group represents an (alkyl (having 1 to 10carbon atoms))-S—C(═O)— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include methylthiocarbonyl andethylthiocarbonyl.

The C₁-C₆ alkoxycarbonyloxy group represents an oxy group substitutedwith an (alkoxy (having 1 to 6 carbon atoms))-C(═O)— group, wherein thealkoxycarbonyl moiety has the same definition as above, and examplesthereof include methoxycarbonyloxy and ethoxycarbonyloxy.

The C₁-C₆ haloalkylcarbonyl group represents a (haloalkyl (having 1 to 6carbon atoms))-C(═O)— group, wherein the haloalkyl moiety has the samedefinition as above, and examples thereof include chloroacetyl,trifluoroacetyl, pentafluoropropionyl, and difluoromethylthio.

The C₁-C₆ haloalkylthio group represents a (haloalkyl (having 1 to 6carbon atoms))-S-group, wherein the haloalkyl moiety has the samedefinition as above, and examples thereof include difluoromethylthio andtrifluoromethylthio.

The C₁-C₆ haloalkylsulfinyl group represents a (haloalkyl (having 1 to 6carbon atoms))-SO-group, wherein the haloalkyl moiety has the samedefinition as above, and examples thereof includetrifluoromethylsulfinyl and difluoromethylsulfinyl.

The C₁-C₆ haloalkylsulfonyl group represents a (haloalkyl (having 1 to 6carbon atoms))-SO₂— group, wherein the haloalkyl moiety has the samedefinition as above, and examples thereof include chloromethylsulfonyl,difluoromethylsulfonyl, and trifluoromethylsulfonyl.

The C₃-C₆ haloalkylsulfonyloxy group represents a (haloalkyl (having 1to 6 carbon atoms))-SO₂—O— group, wherein the haloalkyl moiety has thesame definition as above, and examples thereof includechloromethylsulfonyloxy and trifluoromethylsulfonyloxy.

The mono(C₁-C₆ alkyl)aminocarbonyl group represents an (alkyl (having 1to 6 carbon atoms))-NH—C(═O)— group, wherein the alkyl moiety has thesame definition as above, and examples thereof includemethylaminocarbonyl and ethylaminocarbonyl.

The di(C₁-C₆ alkyl)aminocarbonyl group represents an (alkyl (having 1 to6 carbon atoms))₂N—C(═O)— group, wherein the alkyl moiety has the samedefinition as above, and examples thereof include a group likedimethylaminocarbonyl, diethylaminocarbonyl, methylethylaminocarbonyl,dipropylaminocarbonyl, and dibutylaminocarbonyl.

The cyano C₁-C₆ alkyl group represents a cyano alkyl group having 1 to 6carbon atoms, wherein the alkyl moiety has the same definition as above,and examples thereof include cyanomethyl and cyanoethyl.

The cyano C₁-C₆ alkoxy group represents an alkoxy group having 1 to 6carbon atoms substituted with a cyano group, wherein the alkoxy moietyhas the same definition as above, and examples thereof include a grouplike 2-cyanoethoxy and 3-cyanopropoxy.

The cyano C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specifiedotherwise, an alkyl group having 1 to 6 carbon atoms substituted with analkoxy group having 1 to 6 carbon atoms substituted with a cyano group,wherein the alkoxy moiety and alkyl moiety have the same definitions asabove, and examples thereof include a group like 2-cyanoethoxymethyl and3-cyanopropoxymethyl.

The phenyl C₁-C₆ alkyl group represents an alkyl group having 2 to 6carbon atoms substituted with a phenyl group, wherein the alkyl moietyhas the same definition as above, and examples thereof include benzyl,phenethyl, and phenylpropyl.

The phenyl C₂-C₆ alkenyl group represents an alkenyl group having 2 to 6carbon atoms substituted with a phenyl group, wherein the alkenyl moietyhas the same definition as above, and examples thereof include styryland cinnamyl.

The phenyl C₂-C₆ alkynyl group represents an alkynyl group having 2 to 6carbon atoms substituted with a phenyl group, wherein the alkynyl moietyhas the same definition as above, and examples thereof include(2-phenyl)ethynyl and 2-(3-phenyl)ethynyl.

The phenylcarbonyloxy group represents a (phenyl)-C(═O)—O— group andexamples thereof include a phenylcarbonyloxy group.

The phenylcarbonyl C₁-C₆ alkyloxy group represents an alkoxy grouphaving 1 to 6 carbon atoms substituted with a (phenyl)-C(═O) group andexamples thereof include phenylcarbonylmethoxy.

The phenylthio group represents a phenyl-S— group.

The phenylsulfinyl group represents a phenyl-SO— group.

The phenylsulfonyl group represents a phenyl-SO₂— group.

The phenylsulfonyloxy group represents a phenyl-SO₂—O— group.

The benzylthio group represents a benzyl-S— group.

The benzylsulfinyl group represents a benzyl-SO— group.

The benzylsulfonyl group represents a benzyl-SO₂— group.

The benzylsulfonyloxy group represents a benzyl-SO₂—O— group.

As a group constituting a C₃-C₆ alkylene group, 1 to 3 carbon atoms inthe alkylene group may be substituted with an atom selected from a groupconsisting of an oxygen-atom, a sulfur atom, a nitrogen atom, and acarbon atom constituting a carbonyl group, and the C₃-C₆ alkylene groupis a linear or branched divalent alkylene group having 3 to 6 carbonatoms, and 1 to 3 carbon atoms in the alkylene group may be substitutedwith an atom or a group of atoms selected from a group consisting of anoxygen atom, a sulfur atom, a nitrogen atom, and a carbon atomconstituting a carbonyl group, and examples thereof include atrimethylene group, a propylene group, a butylene group, amethylenedioxy group, and an ethylenedioxy group. Preferred examples ofthe alkylene group include a C₁-C₃ alkylenedioxy group.

Examples of the heterocyclic group having 3 to 10 carbon atoms and oneor more heteroatoms that are the same or different from each other andselected from an oxygen atom, a sulfur atom, and a nitrogen atom includefuran, thiophene, pyrrole, pyrazole, imidazole, pyridine, pyrimidine,pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, morpholine,thiomorpholine, benzofuran, benzothiophene, indole, benzoxazole,benzothiazole, benzimidazole, isoxazole, isoxazoline, oxazole,oxazoline, isothiazole, isothiazoline, thiazole, thetrahydrofuran, andthiazoline. Preferred examples of the heterocyclic group includepyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole,morpholine, thiomorpholine (sulfur atom of thiomorpholine may be bondedwith one or two oxygen atoms), piperidine, pyridazine, piperazine, andtetrahydrofuran. More preferred examples of the heterocyclic groupinclude pyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole,morpholine, thiomorpholine (sulfur atom of thiomorpholine may be bondedwith one or two oxygen atoms), and piperidine.

The heterocyclic oxy group having 3 to 10 carbon atoms and one or moreheteroatoms that are the same or different from each other andoptionally selected from an oxygen atom, a sulfur atom, and a nitrogenatom represents, unless specified otherwise, a group in which the oxygenatom is substituted with a heterocycle having the same definition asabove, and examples thereof include (tetrahydrofuran-2-yl)oxy,(4,5-dihydroisoxazol-5-yl)oxy, (isoxazol-5-yl)oxy, and a(thiophen-2-yl)oxy group.

The C₁-C₆ alkyl group substituted with a heterocyclic group having 3 to10 carbon atoms and one or more heteroatoms that are the same ordifferent from each other and selected from an oxygen atom, a sulfuratom, and a nitrogen atom represents an alkyl group having 1 to 6 carbonatoms substituted with a heterocycle wherein the alkyl moiety andheterocyclic moiety have the same definitions as above, and examplesthereof include (2-furan)methyl, (3-furan)methyl, (2-thiophene)methyl,and (3-thiophene)methyl.

The C₁-C₆ alkyl group substituted with a heterocyclic oxy group having 3to 10 carbon atoms and one or more heteroatoms that are the same ordifferent from each other and selected from an oxygen atom, a sulfuratom, and a nitrogen atom represents an alkyl group having 1 to 6 carbonatoms substituted with a heterocyclic oxy group wherein the alkyl moietyand heterocyclic moiety have the same definitions as above, and examplesthereof include (tetrahydrofuran-2-yl)oxymethyl,(4,5-dihydroisoxazol-5-yl)oxymethyl, (isoxazol-5-yl)oxymethyl, and(thiophen-2-yl)oxymethyl.

The C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic oxygroup having 3 to 10 carbon atoms and one or more heteroatoms that arethe same or different from each other and selected from an oxygen atom,a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to6 carbon atoms substituted with an alkoxy group having 1 to 6 carbonatoms substituted with a heterocyclic oxy group wherein the alkylmoiety, alkoxy moiety, and heterocyclic moiety have the same definitionsas above, and examples thereof include(tetrahydrofuran-2-yl)oxymethoxymethyl,(4,5-dihydroisoxazol-5-yl)oxyethoxymethyl,(isoxazol-5-yl)oxymethoxymethyl, and (thiophen-2-yl)oxyethoxymethyl.

The C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic grouphaving 3 to 10 carbon atoms and one or more heteroatoms that are thesame or different from each other and selected from an oxygen atom, asulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6carbon atoms substituted with an alkoxy group having 1 to 6 carbon atomssubstituted with a heterocyclic group wherein the alkyl moiety, alkoxymoiety, and heterocyclic moiety have the same definitions as above, andexamples thereof include tetrahydrofurfuryloxyethyl andtetrahydrofurfuryloxymethyl.

The C₁-C₆ alkoxy group substituted with a heterocyclic group having 3 to10 carbon atoms and one or more heteroatoms that are the same ordifferent from each other and selected from an oxygen atom, a sulfuratom, and a nitrogen atom represents an alkoxy group having 1 to 6carbon atoms substituted with a heterocyclic group wherein theheterocyclic moiety and alkoxy moiety have the same definitions asabove, and examples thereof include a 6-methyl-2-pyridinemethoxy groupand a tetrahydrofurfuryloxy group.

Alkali metal includes sodium, potassium, and the like.

Next, specific examples of the compound of the invention represented byFormula 1 are described in Table 1 to Table 43. However, the inventionis not limited to those compounds.

In the present Description, the following descriptions included in thetables indicate the corresponding group, respectively, as shown below.

For example, Me represents a methyl group, Et represents an ethyl group,Pr-n represents a n-propyl group, Pr-i represents an isopropyl group,Pr-c represents a cyclopropyl group, Bu-n represents a n-butyl group,Bu-s represents a secondary butyl group, Bu-i represents an isobutylgroup, Bu-t represents a tertiary butyl group, Bu-c represents acyclobutyl group, Pen-n represents a n-pentyl group, Pen-c represents acyclopentyl group, Hex-n represents a n-hexyl group, Hex-c represents acyclohexyl group, Ac represents an acetyl group, Ph represents a phenylgroup, Bn represents a benzyl group, Ts represents a p-toluene sulfonylgroup, pyridyl represents a pyridyl group, and pyrimidinyl represents apyrimidinyl group. Further, Ph(2-OMe) represents a 2-methoxyphenylgroup, CH₂Ph(2-OMe) represents a 2-methoxybenzyl group, and Ph(3,4-C₁₂)represents a 3,4-dichlorophenyl group.

TABLE 1

Com- pound No. R¹ R² Y Z R⁴ I-1  Me Me O O OH I-2  Et Me O O OH I-3 Pr-n Me O O OH I-4  Pr-i Me O O OH I-5  Bu-n Me O O OH I-6  Bu-i Me O OOH I-7  Bu-s Me O O OH I-8  Bu-t Me O O OH I-9  Hex-n Me O O OH I-10CH₂CF₃ Me O O OH I-11 CH₂CH═CH₂ Me O O OH I-12 CH₂C(Me)═CH₂ Me O O OHI-13 CH₂CH₂CH═CMe₂ Me O O OH I-14 CH₂C≡CH Me O O OH I-15 CH₂C≡CCH₃ Me OO OH I-16 Pr-c Me O O OH I-17 Bu-c Me O O OH I-18 Pen-c Me O O OH I-19Hex-c Me O O OH I-20 CH₂Pr-c Me O O OH I-21 CH₂Bu-c Me O O OH I-22CH₂Pen-c Me O O OH I-23 CH₂Hex-c Me O O OH I-24 CH₂CH═CCl₂ Me O O OHI-25 CH₂CCl═CHCl Me O O OH I-26 CH₂CH₂CH═CCl₂ Me O O OH I-27CH₂CH₂C(Me)═CF₂ Me O O OH I-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O OH I-29CH₂CH═CF₂ Me O O OH I-30 CH₂CH₂OMe Me O O OH I-31 CH₂CH₂OEt Me O O OHI-32 CH(Me)CH₂OMe Me O O OH I-33 CH₂CH₂OCH₂CH₂OMe Me O O OH I-34CH₂CH₂OPr-n Me O O OH I-35 CH₂CH₂OPr-i Me O O OH I-36 CH₂CH₂OPr-c Me O OOH I-37 CH₂CH₂OBu-c Me O O OH I-38 CH₂CH₂OPen-c Me O O OH I-39CH₂CH₂OHex-c Me O O OH I-40 CH₂CH₂OCH₂CF₃ Me O O OH I-41 CH₂CH₂CH₂OMe MeO O OH

TABLE 2 Compound No. R¹ R² Y Z R⁴ I-42 CH═CHMe Me O O OH I-43 CH₂SMe MeO O OH I-44 CH₂SPr-n Me O O OH I-45 CH₂CH₂SMe Me O O OH I-46 CH₂SOMe MeO O OH I-47 CH₂SO₂Me Me O O OH I-48 CH₂CH₂CH₂SMe Me O O OH I-49CH₂CH₂CH₂SO₂Me Me O O OH I-50 Ph Me O O OH I-51 Ph(2-Cl) Me O O OH I-52Ph(3-Cl) Me O O OH I-53 Ph(4-Cl) Me O O OH I-54 Ph(2-F) Me O O OH I-55Ph(3-F) Me O O OH I-56 Ph(4-F) Me O O OH I-57 Ph(2-Me) Me O O OH I-58Ph(3-Me) Me O O OH I-59 Ph(4-Me) Me O O OH I-60 Ph(2-OMe) Me O O OH I-61Ph(3-OMe) Me O O OH I-62 Ph(4-OMe) Me O O OH I-63 Ph(2-CF₃) Me O O OHI-64 Ph(3-CF₃) Me O O OH I-65 Ph(4-CF₃) Me O O OH I-66 Ph(2-NO₂) Me O OOH I-67 Ph(3-NO₂) Me O O OH I-68 Ph(4-NO₂) Me O O OH I-69 Ph(2-OCF₃) MeO O OH I-70 Ph(3-OCF₃) Me O O OH I-71 Ph(4-OCF₃) Me O O OH I-72 Ph(2-CN)Me O O OH I-73 Ph(3-CN) Me O O OH I-74 Ph(4-CN) Me O O OH I-75Ph(3,4-F₂) Me O O OH I-76 Ph(3,5-F₂) Me O O OH I-77 Ph(2,3-F₂) Me O O OHI-78 Ph(2,4-F₂) Me O O OH I-79 Ph(2,5-F₂) Me O O OH I-80 Ph(2,6-F₂) Me OO OH I-81 Ph(3,4-Cl₂) Me O O OH I-82 Ph(3,5-Cl₂) Me O O OH I-83Ph(2,3-Cl₂) Me O O OH I-84 Ph(2,4-Cl₂) Me O O OH I-85 Ph(2,5-Cl₂) Me O OOH

TABLE 3 Compound No. R¹ R² Y Z R⁴ I-86 Ph(2,6-Cl₂) Me O O OH I-87Ph(3,4-Me₂) Me O O OH I-88 Ph(3,5-Me₂) Me O O OH I-89 Ph(2,3-Me₂) Me O OOH I-90 Ph(2,4-Me₂) Me O O OH I-91 Ph(2,5-Me₂) Me O O OH I-92Ph(2,6-Me₂) Me O O OH I-93 Ph(3,4-OMe₂) Me O O OH I-94 Ph(3,5-OMe₂) Me OO OH I-95 Ph(2,3-OMe₂) Me O O OH I-96 Ph(2,4-OMe₂) Me O O OH I-97Ph(2,5-OMe₂) Me O O OH I-98 Ph(2,6-OMe₂) Me O O OH I-99 Ph(3-F-4-OMe) MeO O OH I-100 Ph(3-F-5-OMe) Me O O OH I-101 Ph(2-F-3-OMe) Me O O OH I-102Ph(2-F-4-OMe) Me O O OH I-103 Ph(2-F-5-OMe) Me O O OH I-104Ph(2-F-6-OMe) Me O O OH I-105 Ph(3-F-4-Me) Me O O OH I-106 Ph(3-F-5-Me)Me O O OH I-107 Ph(2-F-3-Me) Me O O OH I-108 Ph(2-F-4-Me) Me O O OHI-109 Ph(2-F-5-Me) Me O O OH I-110 Ph(2-F-6-Me) Me O O OH I-111Ph(3-OMe-4-F) Me O O OH I-112 Ph(2-OMe-3-F) Me O O OH I-113Ph(2-OMe-4-F) Me O O OH I-114 Ph(2-OMe-5-F) Me O O OH I-115 Ph(3-Me-4-F)Me O O OH I-116 Ph(2-Me-3-F) Me O O OH I-117 Ph(2-Me-4-F) Me O O OHI-118 Ph(2-Me-5-F) Me O O OH I-119 Ph(3-Cl-4-OMe) Me O O OH I-120Ph(3-Cl-5-OMe) Me O O OH I-121 Ph(2-Cl-3-OMe) Me O O OH I-122Ph(2-Cl-4-OMe) Me O O OH I-123 Ph(2-Cl-5-OMe) Me O O OH I-124Ph(2-Cl-6-OMe) Me O O OH I-125 Ph(3-Cl-4-Me) Me O O OH I-126Ph(3-Cl-5-Me) Me O O OH I-127 Ph(2-Cl-3-Me) Me O O OH I-128Ph(2-Cl-4-Me) Me O O OH I-129 Ph(2-Cl-5-Me) Me O O OH

TABLE 4 Compound No. R¹ R² Y Z R⁴ I-130 Ph(2-Cl-6-Me) Me O O OH I-131Ph(3-OMe-4-Cl) Me O O OH I-132 Ph(2-OMe-3-Cl) Me O O OH I-133Ph(2-OMe-4-Cl) Me O O OH I-134 Ph(2-OMe-5-Cl) Me O O OH I-135Ph(3-Me-4-Cl) Me O O OH I-136 Ph(2-Me-3-Cl) Me O O OH I-137Ph(2-Me-4-Cl) Me O O OH I-138 Ph(2-Me-5-Cl) Me O O OH I-139 Ph(3-F-4-Cl)Me O O OH I-140 Ph(3-F-5-Cl) Me O O OH I-141 Ph(2-F-3-Cl) Me O O OHI-142 Ph(2-F-4-Cl) Me O O OH I-143 Ph(2-F-5-Cl) Me O O OH I-144Ph(2-F-6-Cl) Me O O OH I-145 Ph(3-Cl-4-F) Me O O OH I-146 Ph(2-Cl-3-F)Me O O OH I-147 Ph(2-Cl-4-F) Me O O OH I-148 Ph(2-Cl-5-F) Me O O OHI-149 Ph(3-Me-4-OMe) Me O O OH I-150 Ph(3-Me-5-OMe) Me O O OH I-151Ph(2-Me-3-OMe) Me O O OH I-152 Ph(2-Me-4-OMe) Me O O OH I-153Ph(2-Me-5-OMe) Me O O OH I-154 Ph(2-Me-6-OMe) Me O O OH I-155Ph(3-OMe-4-Me) Me O O OH I-156 Ph(2-OMe-3-Me) Me O O OH I-157Ph(2-OMe-4-Me) Me O O OH I-158 Ph(2-OMe-5-Me) Me O O OH I-159Ph(3-CN-4-OMe) Me O O OH I-160 Ph(3-OMe-4-CN) Me O O OH I-161Ph(3-Me-4-CN) Me O O OH I-162 Ph(3-CN-4-Me) Me O O OH I-163Ph(3-NO₂-4-OMe) Me O O OH I-164 Ph(3-OMe-4-NO₂) Me O O OH I-165Ph(3-Me-4-NO₂) Me O O OH I-166 Ph(3-NO₂-4-Me) Me O O OH I-167Ph(3,5-F₂-4-OMe) Me O O OH I-168 Ph(3,5-F₂-4-Me) Me O O OH I-169Ph(3,4,5-(OMe)₃) Me O O OH

TABLE 5 Compound No. R¹ R² Y Z R⁴ I-170

Me O O OH I-171

Me O O OH I-172

Me O O OH I-173

Me O O OH I-174

Me O O OH I-175

Me O O OH I-176

Me O O OH I-177

Me O O OH I-178

Me O O OH I-179

Me O O OH I-180

Me O O OH I-181

Me O O OH I-182

Me O O OH I-183

Me O O OH I-184

Me O O OH

TABLE 6 Compound No. R¹ R² Y Z R⁴ I-185

Me O O OH I-186

Me O O OH I-187

Me O O OH I-188

Me O O OH I-189

Me O O OH I-190

Me O O OH I-191

Me O O OH I-192

Me O O OH I-193

Me O O OH I-194

Me O O OH I-195

Me O O OH I-196

Me O O OH I-197

Me O O OH I-198

Me O O OH I-199

Me O O OH I-200

Me O O OH

TABLE 7 Compound No R¹ R² Y Z R⁴ I-201

Me O O OH I-202

Me O O OH I-203

Me O O OH I-204

Me O O OH I-205 CH₂Ph Me O O OH I-206 CH₂CH₂Ph Me O O OH I-207CH₂CH₂CH₂Ph Me O O OH I-208 CH₂CH═CHPh Me O O OH I-209 CH₂C≡CPh Me O OOH I-210 CH₂CH═NOMe Me O O OH I-211 CH₂CH═NOEt Me O O OH I-212CH₂CH═NOPr-n Me O O OH I-213 CH₂CH═NOPh Me O O OH I-214 CH₂CH(OMe)₂ Me OO OH I-215 CH₂CHO Me O O OH I-216 NH₂ Me O O OH I-217 NHMe Me O O OHI-218 NHEt Me O O OH I-219 NHPr-n Me O O OH I-220 NHPr-i Me O O OH I-221NHBu-n Me O O OH I-222 NHBu-i Me O O OH I-223 NHBu-s Me O O OH I-224NHCH₂Pr-c Me O O OH I-225 NHPen-n Me O O OH I-226 NHHex-n Me O O OHI-227 NHCH₂CH₂CH₂Cl Me O O OH I-228 NHCH₂CH₂CH₂F Me O O OH I-229NHCH₂CH₂OMe Me O O OH I-230 NMe₂ Me O O OH I-231 NEt₂ Me O O OH I-232N(Pr-n)₂ Me O O OH I-233 N(Bu-n)₂ Me O O OH I-234 N(Me)Et Me O O OHI-235 N(Me)CH₂CH₂OMe Me O O OH I-236 NHPh Me O O OH I-237 NHCH₂Ph Me O OOH I-238 N═CMe₂ Me O O OH I-239 N═CEt₂ Me O O OH

TABLE 8 Compound No. R¹ R² Y Z R⁴ I-240 N═CHNMe₂ Me O O OH I-241NHC(═O)Me Me O O OH I-242 N[C(═O)Me]₂ Me O O OH I-243 NHC(═O)OMe Me O OOH I-244 N[C(═O)OMe]₂ Me O O OH I-245 NHSO₂Me Me O O OH I-246 NHSO₂Ph MeO O OH I-247 NHSO₂CH₂Ph Me O O OH I-248 OMe Me O O OH I-249 OEt Me O OOH I-250 OPr-n Me O O OH I-251 OPr-i Me O O OH I-252 OCH₂Pr-c Me O O OHI-253 OCH₂Cl Me O O OH I-254 OCHCl₂ Me O O OH I-255 OCCl₃ Me O O OHI-256 OCH₂F Me O O OH I-257 OCHF₂ Me O O OH I-258 OCF₃ Me O O OH I-259Ph Et O O OH I-260 Ph Pr-i O O OH I-261 Ph CHF₂ O O OH I-262 Ph Ph O OOH I-263 Ph Me O S OH I-264 Ph Me S S OH I-265 Me Me O S OH I-266 Me MeS S OH I-267 Ph Me O O SPh I-268 Ph(4-OEt) Me O O OH I-269 Ph(2-Ph) Me OO OH I-270 Ph(3-Ph) Me O O OH I-271 Ph(4-Ph) Me O O OH I-272

Me O O OH I-273

Me O O OH I-274 Me

O O OH I-275 Et

O O OH I-276

Me O O OH

TABLE 9 Compound No. R¹ R² Y Z R⁴ I-277

Me O O OH I-278

Me O O OH I-279

Me O O OH I-280

Me O O OH I-281

Me O O OH I-282 Ph(2-Me-4-Br) Me O O OH I-283 Ph(2-Me-4-I) Me O O OHI-284 Ph(2-Me-5-CF₃) Me O O OH I-285 Ph(2-Me-6-OCF₃) Me O O OH I-286Ph(2-Pr-i) Me O O OH I-287

Me O O OH I-288 Ph(2-Et) Me O O OH I-289

Me O O OH I-290

Me O O OH I-291

Me O S OH I-292

Me O O OH I-293

Me O O OH I-294 CH₂COOBu-t Me O O OH I-295 (C₇H₁₄)CH₃ Me O O OH I-296(C₉H₁₈)CH₃ Me O O OH I-297 Ph(2-F,4-Cl,5-OMe) Me O O OH I-298Ph(2,3,4-(OMe)₃ Me O O OH I-299 Ph(3,5-Cl₂-4-OMe) Me O O OH I-300Ph(3,5-Cl₂-4-SMe) Me O O OH I-301 Ph(3,5-Cl₂-4-SO₂Me) Me O O OH I-302Ph(3,4,5-F₃) Me O O OH I-303

Me O O OH

TABLE 10 Com- pound No. R¹ R² Y Z R⁴ I-304

Me O O OH I-305

Me O O OH I-306 Bu-n

O O OH I-307 CH₂CH(CH₃)₂

O O OH I-308 Ph Pen-n O O OH I-309 H Me O O OH I-310 CH₂C≡CF Me O O OHI-311

Me O O OH I-312

Me O O OH I-313 CH₂NH₂ Me O O OH I-314 CH₂NO₂ Me O O OH I-315 CH₂NHCH₃Me O O OH I-316 CH₂N(CH₃)₂ Me O O OH I-317 CH₂SCH₂CF₃ Me O O OH I-318CH₂SOCH₂CF₃ Me O O OH I-319 CH₂SO₂CH₂CF₃ Me O O OH I-320 CH₂OH Me O O OHI-321 CH₂OBn Me O O OH I-322 CH₂OCH₂Pr-c Me O O OH I-323 CH₂OPh Me O OOH I-324 CH₂SPh Me O O OH I-325 CH₂SOPh Me O O OH I-326 CH₂SO₂Ph Me O OOH I-327 CH₂CON(CH₃)₂ Me O O OH I-328 CH₂COCH₃ Me O O OH I-329 CH₂OCOCH₃Me O O OH I-330 CH₂ON═CHCH₃ Me O O OH I-331 C₂H₄OC₂H₄SCH₃ Me O O OHI-332 C₂H₄OC₂H₄SOCH₃ Me O O OH I-333 C₂H₄OC₂H₄SO₂CH₃ Me O O OH I-334CH₂OCH₂CN Me O O OH I-335 CH₂CN Me O O OH I-336 OCH₂CH═CH₂ Me O O OHI-337 OCH₂C≡CH Me O O OH I-338 OPr-c Me O O OH

TABLE 11 Compound No. R¹ R² Y Z R⁴ I-339

Me O O OH I-340

Me O O OH I-341

Me O O OH I-342

Me O O OH I-343

Me O O OH I-344 Ph H O O OH I-345 Ph CH₂CH═CH₂ O O OH I-346 Ph CH₂C≡CH OO OH I-347 Ph Pr-c O O OH I-348 Ph CH₂CH═CF₂ O O OH I-349 Ph CH₂C≡CF O OOH I-350 Ph C₂H₄OCH₃ O O OH I-351 Ph C₂H₄OC₂H₅ O O OH I-352 Ph CH(Me)OEtO O OH I-353 Ph CH₂OPr-c O O OH I-354 Ph CH(OCH₃)₂ O O OH I-355 Ph CH₂PhO O OH I-356 Ph

O O OH I-357 Ph

O O OH I-358 Ph Me O O NH₂ I-359 Ph Me O O Cl I-360 Ph Me O O CN I-361Ph Me O O NCS I-362 Ph Me O O NCO I-363 Ph Me O O OCO₂H I-364 Ph Me O OOCO₂CH₃ I-365 Ph Me O O OCO₂CH₂Ph I-366 Ph Me O O OMe I-367 Ph Me O OOEt I-368 Ph Me O O OPr I-369 Ph Me O O OCH₂CH═CH₂ I-370 Ph Me O OOCH₂C≡CH I-371 Ph Me O O OPr-c I-372 Ph Me O O OBu-c I-373 Ph Me O OOPen-c

TABLE 12 Compound No. R¹ R² Y Z R⁴ I-374 Ph Me O O OHex-c I-375 Ph Me OO OCH₂CN I-376 Ph Me O O OCH₂Pr-c I-377 Ph Me O O OCOCH₃ I-378 Ph Me O OOCOCCl₃ I-379 Ph Me O O OCOCH═CH₂ I-380 Ph Me O O OCOCH═CF₂ I-381 Ph MeO O OCOCH₂C≡CH I-382 Ph Me O O OCOCH₂C≡CF I-383 Ph Me O O OCH₂CO₂CH₃I-384 Ph Me O O OPh I-385 Ph Me O O OCH₂Ph I-386 Ph Me O O OCOPh I-387Ph Me O O OCOCH₂Ph I-388 Ph Me O O OCH₂COPh I-389 Ph Me O O OSO₂CH₂CF₃I-390 Ph Me O O OSO₂CH₂Ph I-391 Ph Me O O SCH₃ I-392 Ph Me O O SOCH₃I-393 Ph Me O O SO₂CH₃ I-394 Ph Me O O SCH₂CF₃ I-395 Ph Me O O SOCH₂CF₃I-396 Ph Me O O SO₂CH₂CF₃ I-397 Ph Me O O SCH₂CH═CH₂ I-398 Ph Me O OSOCH₂CH═CH₂ I-399 Ph Me O O SO₂CH₂CH═CH₂ I-400 Ph Me O O SCH₂CH≡CH I-401Ph Me O O SOCH₂CH≡CH I-402 Ph Me O O SO₂CH₂CH≡CH I-403 Ph Me O O SCH₂PhI-404 Ph Me O O SOPh I-405 Ph Me O O SOCH₂Ph I-406 Ph Me O O SO₂Ph I-407Ph Me O O SO₂CH₂Ph I-408 Ph Me O O NHCH₃ I-409 Ph Me O O N(CH₃)₂ I-410Ph Me O O NHCOCH₃ I-411 Ph Me O O

I-412 Ph Me O O

TABLE 13 Compound No. R¹ R² Y Z R⁴ I-413 Ph Me O O

I-414 Ph Me O O

I-415 Ph Me O O

I-416 Ph Me O O

I-417 (4-Pr-c)Ph Me O O OH I-418 (4-CH₂Pr-c)Ph Me O O OH I-419(4-CH₂═CHCH₂)Ph Me O O OH I-420 (4-CH≡CCH₂)Ph Me O O OH I-421(4-CH₂CH═CF₂)Ph Me O O OH I-422 (4-CH₂CH≡CF)Ph Me O O OH I-423

Me O O OH I-424

Me O O OH I-425

Me O O OH I-426

Me O O OH I-427

Me O O OH I-428

Me O O OH I-429 (4-OCHF₂)Ph Me O O OH I-430 (4-SMe)Ph Me O O OH I-431(4-SOMe)Ph Me O O OH I-432 (4-SO₂Me)Ph Me O O OH I-433 (4-SCF₃)Ph Me O OOH I-434 (4-SOCF₃)Ph Me O O OH I-435 (4-SO₂CF₃)Ph Me O O OH I-436

Me O O OH I-437

Me O O OH

TABLE 14 Compound No. R¹ R² Y Z R⁴ I-438

Me O O OH I-439

Me O O OH I-440

Me O O OH I-441

Me O O OH I-442

Me O O OH I-443

Me O O OH I-444

Me O O OH I-445

Me O O OH I-446

Me O O OH I-447

Me O O OH I-448

Me O O OH I-449

Me O O OH I-450

Me O O OH I-451

Me O O OH I-452

Me O O OH I-453

Me O O OH I-454

Me O O OH I-455

Me O O OH

TABLE 15 Com- pound No. R¹ R² Y Z R⁴ I-456

Me O O OH I-457

Me O O OH I-458

Me O O OH I-459

Me O O OH I-460

Me O O OH I-461

Me O O OH I-462

Me O O OH I-463

Me O O OH I-464

Me O S OH I-465 Ph(3,4,5-Cl) Me O O OH I-466 N(Me)Ph Me O O OH I-467

Me O O OH I-468 CH₂CO(Bu-t) Me O O OH I-469 Ph(2,3,5,6-F₄) Me O O OHI-470 Ph[(3,5-(CF₃)₂] Me O O OH I-471 CH₂C(Me)═NOMe Me O O OH I-472Ph(2,4,6-Me₃) Me O O OH I-473 Ph(2,3,4,5,6-F₅) Me O O OH I-474 N(Et)PhMe O O OH I-475 N(Pr-i)Ph Me O O OH I-476 N(Me)Ph(4-F) Me O O OH I-477Ph CH₂CF₃ O O OH I-478 CH₂C(Me)═NOEt Me O O OH I-479 CH₂C(Me)═NO(Pr-i)Me O O OH I-480 Ph(4-F) Me O S OH

TABLE 16

Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-1 Me Me O O Me H OH II-2 Et Me OO Me Me OH II-3 Pr-n Me O O Me H OH II-4 Pr-i Me O O Me H OH II-5 Bu-nMe O O Me H OH II-6 Bu-i Me O O Me H OH II-7 Bu-s Me O O Me Me OH II-8Bu-t Me O O Me H OSO₂Pr II-9 Hex-n Me O O Me H OH II-10 CH₂CF₃ Me O O MeH OH II-11 CH₂CH═CH₂ Me O O Et H OH II-12 CH₂C(Me)═CH₂ Me O O Me H OHII-13 CH₂CH₂CH═CMe₂ Me O O Me H OH II-14 CH₂C≡CH Me O O Me Me OH II-15CH₂C≡CCH₃ Me O O Me H OSO₂Ph II-16 Pr-c Me O O Me H OH II-17 Bu-c Me O Oi-Pr H OH II-18 Pen-c Me O O Me H OH II-19 Hex-c Me O O Et H OH II-20CH₂Pr-c Me O O Me H OH II-21 CH₂Bu-c Me O O Me H OH II-22 CH₂Pen-c Me OO Me Me OH II-23 CH₂Hex-c Me O O Me H OH II-24 CH₂CH═CCl₂ Me O O Me HOSO₂Pr II-25 CH₂CCl═CHCl Me O O Me H OH II-26 CH₂CH₂CH═CCl₂ Me O O Et HOH II-27 CH₂CH₂C(Me)═CF₂ Me O O Me H OH II-28 CH₂CH₂CH₂- Me O O Me H OHCH₂C(Me)═CF₂ II-29 CH₂CH═CF₂ Me O O Me Me OH II-30 CH₂CH₂OMe Me O O Me HOH II-31 CH₂CH₂OEt Me O O Me H OH II-32 CH(Me)CH₂OMe Me O O Pr-i H OHII-33 CH₂CH₂OCH₂CH₂OMe Me O O Me H OH II-34 CH₂CH₂OPr-n Me O O Et H OHII-35 CH₂CH₂OPr-i Me O O Me H OH II-36 CH₂CH₂OPr-c Me O O Me Me OH II-37CH₂CH₂OBu-c Me O O Me H OH II-38 CH₂CH₂OPen-c Me O O Me H OH II-39CH₂CH₂OHex-c Me O O Me H OH

TABLE 17 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-40 CH₂CH₂OCH₂CF₃ Me O O EtMe OH II-41 CH₂CH₂CH₂OMe Me O O Me H OH II-42 CH═CHMe Me O O Me H OSO₂PhII-43 CH₂SMe Me O O Me H OH II-44 CH₂SPr-n Me O O Me H OH II-45CH₂CH₂SMe Me O O Pr-i H OH II-46 CH₂CH₂SOMe Me O O Me H OH II-47CH₂CH₂SO₂Me Me O O Me Me OH II-48 CH₂CH₂CH₂SMe Me O O Et H OH II-49CH₂CH₂CH₂SO₂Me Me O O Me H OH II-50 Ph Me O O Me H OH II-51 Ph(2-Cl) MeO O Me H OH II-52 Ph(3-Cl) Me O O Me H OH II-53 Ph(4-C1) Me O O Me HOSO₂Pr II-54 Ph(2-F) Me O O Pr-i H OH II-55 Ph(3-F) Me O O Me H OH II-56Ph(4-F) Me O O Me H OH II-57 Ph(2-Me) Me O O Me Me OH II-58 Ph(3-Me) MeO O Me H OH II-59 Ph(4-Me) Me O O Et H OH II-60 Ph(2-OMe) Me O O Me H OHII-61 Ph(3-OMe) Me O O Me H OH II-62 Ph(4-OMe) Me O O Me H OH II-63Ph(2-CF₃) Me O O Me H OH II-64 Ph(3-CF₃) Me O O Pr-i H OSO₂Ph II-65Ph(4-CF₃) Me O O Me H OH II-66 Ph(2-NO₂) Me O O Me H OH II-67 Ph(3-NO₂)Me O O Me H OH II-68 Ph(4-NO₂) Me O O Me Me OH II-69 Ph(2-OCF₃) Me O OMe H OH II-70 Ph(3-OCF₃) Me O O Et H OH II-71 Ph(4-OCF₃) Me O O Me H OHII-72 Ph(2-CN) Me O O Me H OH II-73 Ph(3-CN) Me O O Me H OH II-74Ph(4-CN) Me O O Me H OH II-75 Ph(3,4-F₂) Me O O Pr-i H OH II-76Ph(3,5-F₂) Me O O Me H OH II-77 Ph(2,3-F₂) Me O O Me Me OSO₂Pr II-78Ph(2,4-F₂) Me O O Me H OH II-79 Ph(2,5-F₂) Me O O Me H OH

TABLE 18 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-80 Ph(2,6-F₂) Me O O EtMe OH II-81 Ph(3,4-Cl₂) Me O O Me H OH II-82 Ph(3,5-Cl₂) Me O O Me H OHII-83 Ph(2,3-Cl₂) Me O O Me H OH II-84 Ph(2,4-Cl₂) Me O O Me H OH II-85Ph(2,5-Cl₂) Me O O Pr-i H OH II-86 Ph(2,6-Cl₂) Me O O Me H OH II-87Ph(3,4-Me₂) Me O O Me H OH II-88 Ph(3,5-Me₂) Me O O Me H OH II-89Ph(2,3-Me₂) Me O O Me Me OH II-90 Ph(2,4-Me₂) Me O O Me H OH II-91Ph(2,5-Me₂) Me O O Me H OH II-92 Ph(2,6-Me₂) Me O O Me H OH II-93Ph(3,4-(OMe)₂) Me O O Me H OH II-94 Ph(3,5-(OME)₂) Me O O Me H OH II-95Ph(2,3-(OMe)₂) Me O O Me H OH II-96 Ph(2,4-(OMe)₂) Me O O Pr-i H OHII-97 Ph(2,5-(OMe)₂) Me O O Me H OSO₂Ph II-98 Ph(2,6-(OMe)₂) Me O O Me HOH II-99 Ph(3-F-4-OMe) Me O O Me Me OH II-100 Ph(3-F-5-OMe) Me O O Me HOH II-101 Ph(2-F-3-OMe) Me O O Me H OH II-102 Ph(2-F-4-OMe) Me O O Me HOH II-103 Ph(2-F-5OMe) Me O O Me H OH II-104 Ph(2-F-6-OMe) Me O O Me HOH II-105 Ph(3-F-4-Me) Me O O Me H OSO₂Pr II-106 Ph(3-F-5-Me) Me O O MeH OH II-107 Ph(2-F-3-Me) Me O O Me H OH II-108 Ph(2-F-4-Me) Me O O Me HOH II-109 Ph(2-F-5-Me) Me O O Me Me OH II-110 Ph(2-F-6-Me) Me O O Me HOH II-111 Ph(3-OMe-4-F) Me O O Me H OH II-112 Ph(2-OMe-3-F) Me O O Pr-iH OSO₂Ph(4-Me) II-113 Ph(2-OMe-4-F) Me O O Me H OH II-114 Ph(2-OMe-5-P)Me O O Me H OH II-115 Ph(3-Me-4-F) Me O O Me H OH II-116 Ph(2-Me-3-F) MeO O Me H OH II-117 Ph(2-Me-4-P) Me O O Me H OH II-118 Ph(2-Me-5-F) Me OO Me H OH II-119 Ph(3-Cl-4-OMe) Me O O Me Me OH II-120 Ph(3-Cl-5-OMe) MeO O Me H OH

TABLE 19 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-121 Ph(2-Cl-3-OMe) Me OO Me H OH II-122 Ph(2-Cl-4-OMe) Me O O Me H OSO₂Ph(4-Me) II-123Ph(2-Cl-5-OMe) Me O O Pr-i H OH II-124 Ph(2-Cl-6-OMe) Me O O Me H OHII-125 Ph(3-Cl-4-Me) Me O O Me H OH II-126 Ph(3-Cl-5-Me) Me O O Me Me OHII-127 Ph(2-Cl-3-Me) Me O O Me H OH II-128 Ph(2-Cl-4-Me) Me O O Me H OHII-129 Ph(2-Cl-5-Me) Me O O Me H OH II-130 Ph(2-Cl-6-Me) Me O O Me H OHII-131 Ph(3-OMe-4-Cl) Me O O Me H OH II-132 Ph(2-OMe-3-Cl) Me O O Me HOSO₂Ph II-133 Ph(2-OMe-4-Cl) Me O O Pr-i H OH II-134 Ph(2-OMe-5-Cl) Me OO Me H OH II-135 Ph(3-Me-4-Cl) Me O O Me Me OH II-136 Ph(2-Me-3-Cl) Me OO Me H OH II-137 Ph(2-Me-4-Cl) Me O O Me H OH II-138 Ph(2-Me-5-Cl) Me OO Me H OH II-139 Ph(3-F-4-Cl) Me O O Me H OSO₂Ph(4-Me) II-140Ph(3-F-5-Cl) Me O O Me H OH II-141 Ph(2-F-3-Cl) Me O O Me H OH II-142Ph(2-F-4-Cl) Me O O Me H OH II-143 Ph(2-F-5-Cl) Me O O Me H OH II-144Ph(2-F-6-Cl) Me O O Me H OH II-145 Ph(3-Cl-4-F) Me O O Me H OH II-146Ph(2-Cl-3-F) Me O O Me Me OH II-147 Ph(2-Cl-4-F) Me O O Me H OH II-148Ph(2-Cl-5-F) Me O O Pr-i H OH II-149 Ph(3-Me-4-OMe) Me O O Me H OHII-150 Ph(3-Me-5-OMe) Me O O Me H OH II-151 Ph(2-Me-3-OMe) Me O O Me HOSO₂Ph(4-Me) II-152 Ph(2-Me-4-OMe) Me O O Me H OH II-153 Ph(2-Me-5-OMe)Me O O Me H OH II-154 Ph(2-Me-6-OMe) Me O O Me H OH II-155Ph(3-OMe-4-Me) Me O O Me Me OH II-156 Ph(2-OMe-3-Me) Me O O Me H OHII-157 Ph(2-OMe-4-Me) Me O O Me H OH II-158 Ph(2-OMe-5-Me) Me O O Me MeOH II-159 Ph(3-CN-4-OMe) Me O O Me H OH II-160 Ph(3-OMe-4-CN) Me O O MeH OH II-161 Ph(3-Me-4-CN) Me O O Pr-i H OSO₂Ph(4-Me)

TABLE 20 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-162 Ph(3-CN-4-Me) Me O OMe H OH II-163 Ph(3-NO₂-4-OMe) Me O O Me H OH II-164 Ph(3-OMe-4-NO₂) MeO O Me H OH II-165 Ph(3-Me-4-NO₂) Me O O Me H OH II-166 Ph(3-NO₂-4-Me)Me O O Me H OH II-167 Ph(3,5-F₂-5-OMe) Me O O Me H OH II-168Ph(3,5-F₂-5-Me) Me O O Me Me OH II-169 Ph(3,4,5-(OMe)₃) Me O O Me H OHII-170

Me O O Me H OH II-171

Me O O Me H OH II-172

Me O O Pr-i H OSO₂Ph (4-Me) II-173

Me O O Me H OH II-174

Me O O Me H OH II-175

Me O O Me Me OH II-176

Me O O Me H OH II-177

Me O O Me H OH II-178

Me O O Me H OH II-179

Me O O Me H OH II-180

Me O O Me H OH

TABLE 21 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-181

Me O O Me H OH II-182

Me O O Me H OH II-183

Me O O Me H OH II-184

Me O O Pr-i H OH II-185

Me O O Me Me OH II-186

Me O O Me H OH II-187

Me O O Me H OH II-188

Me O O Me H OH II-189

Me O O Me H OSO₂Ph (4-Me) II-190

Me O O Me H OH II-191

Me O O Me H OH II-192

Me O O Me H OH II-193

Me O O Me H OH II-194

Me O O Me H OH

TABLE 22 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-195

Me O O Me H OH II-196

Me O O Me H OH II-197

Me O O Me H OH II-198

Me O O Me H OH II-199

Me O O Pr-i Me OH II-200

Me O O Me H OH II-201

Me O O Me H OH II-202

Me O O Me H OH II-203

Me O O Me H OH II-204

Me O O Me Me OH II-205 CH₂Ph Me O O Me H OH II-206 CH₂CH₂Ph Me O O Me HOH II-207 CH₂CH₂CH₂Ph Me O O Me H OH II-208 CH₂CH═CHPh Me O O Me H OHII-209 CH₂C≡CPh Me O O Me H OH II-210 CH₂CH═NOMe Me O O Me H OH II-211CH₂CH═NOEt Me O O Me H OH II-212 CH₂CH═NOPr-n Me O O Me H OH II-213CH₂CH═NOPh Me O O Me Me OH II-214 CH₂CH(OMe)₂ Me O O Me H OH II-215CH₂CHO Me O O Et H OH II-216 NH₂ Me O O Me H OH II-217 NHMe Me O O Me HOH II-218 NHEt Me O O Me H OH

TABLE 23 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-219 NHPrn Me O O Me HOSO₂Ph(4-Me) II-220 NHPr-i Me O O Me H OH II-221 NHBu-n Me O O Pr-i H OHII-222 NBiBu-i Me O O Me H OH II-223 NHBu-s Me O O Me Me OH II-224NHCH₂Pr-c Me O O Me H OH II-225 NHPen-n Me O O Me H OH II-226 NHHex-n MeO O Me H OH II-227 NHCH₂CH₂CH₂Cl Me O O Me H OH II-228 NHCH₂CH₂CH₂F Me OO Me H OH II-229 NHCH₂CH₂OMe Me O O Me H OH II-230 NMe₂ Me O O Me H OHII-231 NEt₂ Me O O Me H OH II-232 N(Pr-n)₂ Me O O Me H OH II-233N(Bu-n)₂ Me O O Me H OH II-234 N(Me)Et Me O O Me Me OH II-235N(Me)CH₂CH₂OMe Me O O Et H OH II-236 NHPh Me O O Me H OH II-237 NHCH₂PhMe O O Me H OH II-238 N═CMe₂ Me O O Me H OH II-239 N═CEt₂ Me O O Me HOSO₂Ph(4-Me) II-240 N═CHNMe₂ Me O O Me H OH II-241 NHC(═O)Me Me O O Me HOH II-242 N[C(═O)Me]₂ Me O O Me H OH II-243 NHC(═O)OMe Me O O Pr-i H OHII-244 N[C(═O)OMe]₂ Me O O Me H OH II-245 NHSO₂Me Me O O Me H OH II-246NHSO₂Ph Me O O Me Me OH II-247 NHSO₂CH₂Ph Me O O Me H OH II-248 OMe Me OO Et H OH II-249 OEt Me O O Me H OH II-250 OPr-n Me O O Me H OH II-251OPr-i Me O O Me H OH II-252 OCH₂Pr-c Me O O Me H OH II-253 OCH₂Cl Me O OMe H OH II-254 OCHCl₂ Me O O Me H OH II-255 OCCl₃ Me O O Me Me OH II-256OCH₂F Me O O Me H OH II-257 OCHF₂ Me O O Me H OH II-258 OCF₃ Me O O Me HOSO₂Ph(4-Me) II-259 Ph Et O O Et H OH II-260 Ph Pr-i O O Me H OH II-261Ph CHF₂ O O Me H OH

TABLE 24 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-262 Ph Ph O O Me H OHII-263 Ph Me O S Me Me OH II-264 Ph Me S S Me H OH II-265 Me Me O S Me HOH II-266 Me Me S S Me H OH II-267 Ph Me O O Pr-i H OSO₂Pr II-268Ph(4-OEt) Me O O Me H OH II-269 Ph(2-Ph) Me O O Me H OH II-270 Ph(3-Ph)Me O O Me H OH II-271 Ph(4-Ph) Me O O Me H OH II-272

Me O O Me Me OH II-273

Me O O Et H OSO₂Ph(4-Me) II-274 Me

O O Me H OH II-275 Et

O O Me H OH II-276 H Me O O Me H OH II-277 CH₂C≡CF Me O O Me H OH II-278

Me O O Me H OH II-279

Me O O Me H OH II-280 CH₂NH₂ Me O O Me H OH II-281 CH₂NO₂ Me O O Me H OHII-282 CH₂NHCH₃ Me O O Me H OH II-283 CH₂N(CH₃)₂ Me O O Me H OH II-284CH₂SCH₂CF₃ Me O O Me H OH II-285 CH₂SOCH₂CF₃ Me O O Me H OH II-286CH₂SO₂CH₂CF₃ Me O O Me H OH II-287 CH₂OH Me O O Me H OH II-288 CH₂OBn MeO O Me H OH II-289 CH₂OCH₂Pr-c Me O O Me H OH

TABLE 25 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-290 CH₂OPh Me O O Me H OHII-291 CH₂SPh Me O O Me H OH II-292 CH₂SOPh Me O O Me H OH II-293CH₂SO₂Ph Me O O Me H OH II-294 CH₂CON(CH₃)₂ Me O O Me H OH II-295CH₂COCH₃ Me O O Me H OH II-296 CH₂OCOCH₃ Me O O Me H OH II-297CH₂ON═CHCH₃ Me O O Me H OH II-298 C₂H₄OC₂H₄SCH₃ Me O O Me H OH II-299C₂H₄OC₂H₄SOCH₃ Me O O Me H OH II-300 C₂H₄OC₂H₄SO₂CH₃ Me O O Me H OHII-301 CH₂OCH₂CN Me O O Me H OH II-302 CH₂CN Me O O Me H OH II-303OCH₂CH═CH₂ Me O O Me H OH II-304 OCH₂C≡CH Me O O Me H OH II-305 OPr-c MeO O Me H OH II-306

Me O O Me H OH II-307

Me O O Me H OH II-308

Me O O Me H OH II-309

Me O O Me H OH II-310

Me O O Me H OH II-311 Ph H O O Me H OH II-312 Ph CH₂CH═CH₂ O O Me H OHII-313 Ph CH₂C≡CH O O Me H OH II-314 Ph Pr-c O O Me H OH II-315 PhCH₂CH═CF₂ O O Me H OH II-316 Ph CH₂C≡CF O O Me H OH II-317 Ph C₂H₄OCH₃ OO Me H OH II-318 Ph C₂H₄OC₂H₅ O O Me H OH II-319 Ph CH(Me)OEt O O Me HOH II-320 Ph CH₂OPr-c O O Me H OH II-321 Ph CH(OCH₃)₂ O O Me H OH II-322Ph CH₂Ph O O Me H OH

TABLE 26 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-323 Ph

O O Me H OH II-324 Ph

O O Me H OH II-325 Ph Me O O Me H NH₂ II-326 Ph Me O O Me H Cl II-327 PhMe O O Me H CN II-328 Ph Me O O Me H NCS II-329 Ph Me O O Me H NCOII-330 Ph Me O O Me H OCO₂H II-331 Ph Me O O Me H OCO₂CH₃ II-332 Ph Me OO Me H OCO₂CH₂Ph II-333 Ph Me O O Me H OMe II-334 Ph Me O O Me H OEtII-335 Ph Me O O Me H OPr II-336 Ph Me O O Me H OCH₂CH═CH₂ II-337 Ph MeO O Me H OCH₂C≡CH II-338 Ph Me O O Me H OPr-c II-339 Ph Me O O Me HOBu-c II-340 Ph Me O O Me H OPen-c II-341 Ph Me O O Me H OHex-c II-342Ph Me O O Me H OCH₂CN II-343 Ph Me O O Me H OCH₂Pr-c II-344 Ph Me O O MeH OCOCH₃ II-345 Ph Me O O Me H OCOCCl₃ II-346 Ph Me O O Me H OCOCH═CH₂II-347 Ph Me O O Me H OCOCH═CF₂ II-348 Ph Me O O Me H OCOCH₂C≡CH II-349Ph Me O O Me H OCOCH₂C≡CF II-350 Ph Me O O Me H OCH₂CO₂CH₃ II-351 Ph MeO O Me H OPh II-352 Ph Me O O Me H OCH₂Ph II-353 Ph Me O O Me H OCOPhII-354 Ph Me O O Me H OCOCH₂Ph II-355 Ph Me O O Me H OCH₂COPh II-356 PhMe O O Me H OSO₂CH₂CF₃ II-357 Ph Me O O Me H OSO₂CH₂Ph II-358 Ph Me O OMe H SCH₃ II-359 Ph Me O O Me H SOCH₃ II-360 Ph Me O O Me H SO₂CH₃II-361 Ph Me O O Me H SCH₂CF₃ II-362 Ph Me O O Me H SOCH₂CF₃ II-363 PhMe O O Me H SO₂CH₂CF₃

TABLE 27 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-364 Ph Me O O Me HSCH₂CH═CH₂ II-365 Ph Me O O Me H SOCH₂CH═CH₂ II-366 Ph Me O O Me HSO₂CH₂CH═CH₂ II-367 Ph Me O O Me H SCH₂CH≡CH II-368 Ph Me O O Me HSOCH₂CH≡CH II-369 Ph Me O O Me H SO₂CH₂CH≡CH II-370 Ph Me O O Me HSCH₂Ph II-371 Ph Me O O Me H SOPh II-372 Ph Me O O Me H SOCH₂Ph II-373Ph Me O O Me H SO₂Ph II-374 Ph Me O O Me H SO₂CH₂Ph II-375 Ph Me O O MeH NHCH₃ II-376 Ph Me O O Me H N(CH₃)₂ II-377 Ph Me O O Me H NHCOCH₃II-378 Ph Me O O Me H

II-379 Ph Me O O Me H

II-380 Ph Me O O Me H

II-381 Ph Me O O Me H

II-382 Ph Me O O Me H

II-383 Ph Me O O Me H

TABLE 28

Compound No. R¹ R² Y Z R⁴ III-1 Me Me O O OH III-2 Et Me O O OH III-3Pr-n Me O O OH III-4 Pr-i Me O O OH III-5 Bu-n Me O O OH III-6 Bu-i Me OO OH III-7 Bu-s Me O O OH III-8 Bu-t Me O O OH III-9 Hex-n Me O O OHIII-10 CH₂CF₃ Me O O OH III-11 CH₂CH═CH₂ Me O O OH III-12 CH₂C(Me)═CH₂Me O O OH III-13 CH₂CH₂CH═CMe₂ Me O O OH III-14 CH₂C≡CH Me O O OH III-15CH₂C≡CCH₃ Me O O OH III-16 Pr-c Me O O OH III-17 Bu-c Me O O OH III-18Pen-c Me O O OH III-19 Hex-c Me O O OH III-20 CH₂Pr-c Me O O OH III-21CH₂Bu-c Me O O OH III-22 CH₂Pen-c Me O O OH III-23 CH₂Hex-c Me O O OHIII-24 CH₂CH═CCl₂ Me O O OH III-25 CH₂CCl═CHCl Me O O OH III-26CH₂CH₂CH═CCl₂ Me O O OH III-27 CH₂CH₂C(Me)═CF₂ Me O O OH III-28CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O OH III-29 CH₂CH═CF₂ Me O O OH III-30CH₂CH₂OMe Me O O OH III-31 CH₂CH₂OEt Me O O OH III-32 CH(Me)CH₂OMe Me OO OH III-33 CH₂CH₂OCH₂CH₂OMe Me O O OH III-34 CH₂CH₂OPr-n Me O O OHIII-35 CH₂CH₂OPr-i Me O O OH III-36 CH₂CH₂OPr-c Me O O OH III-37CH₂CH₂OBu-c Me O O OH III-38 CH₂CH₂OPen-c Me O O OH

TABLE 29 Compound No. R¹ R² Y Z R⁴ III-39 CH₂CH₂OHex-c Me O O OH III-40CH₂CH₂OCH₂CF₃ Me O O OH III-41 CH₂CH₂CH₂OMe Me O O OH III-42 CH═CHMe MeO O OH III-43 CH₂SMe Me O O OH III-44 CH₂SPr-n Me O O OH III-45CH₂CH₂SMe Me O O OH III-46 CH₂CH₂SOMe Me O O OH III-47 CH₂CH₂SO₂Me Me OO OH III-48 CH₂CH₂CH₂SMe Me O O OH III 49 CH₂CH₂CH₂SO₂Me Me O O OHIII-50 Ph Me O O OH III-51 Ph(2-Cl) Me O O OH III-52 Ph(3-Cl) Me O O OHIII-53 Ph(4-Cl) Me O O OH III-54 Ph(2-F) Me O O OH III-55 Ph(3-F) Me O OOH III-56 Ph(4-F) Me O O OH III-57 Ph(2-Me) Me O O OH III-58 Ph(3-Me) MeO O OH III-59 Ph(4-Me) Me O O OH III-60 Ph(2-OMe) Me O O OH III-61Ph(3-OMe) Me O O OH III-62 Ph(4-OMe) Me O O OH III-63 Ph(2-CF₃) Me O OOH III-64 Ph(3-CF₃) Me O O OH III-65 Ph(4-CF₃) Me O O OH III-66Ph(2-NO₂) Me O O OH III-67 Ph(3-NO₂) Me O O OH III-68 Ph(4-NO₂) Me O OOH III-69 Ph(2-OCF₃) Me O O OH III-70 Ph(3-OCF₃) Me O O OH III-71Ph(4-OCF₃) Me O O OH III-72 Ph(2-CN) Me O O OH III-73 Ph(3-CN) Me O O OHIII-74 Ph(4-CN) Me O O OH III-75 Ph(3,4-F₂) Me O O OH III-76 Ph(3,5-F₂)Me O O OH III-77 Ph(2,3-F₂) Me O O OH III-78 Ph(2,4-F₂) Me O O OH

TABLE 30 Compound No. R¹ R² Y Z R⁴ III-79 Ph(2,5-F₂) Me O O OH III-80Ph(2,6-F₂) Me O O OH III-81 Ph(3,4-Cl₂) Me O O OH III-82 Ph(3,5-Cl₂) MeO O OH III-83 Ph(2,3-Cl₂) Me O O OH III-84 Ph(2,4-Cl₂) Me O O OH III-85Ph(2,5-Cl₂) Me O O OH III-86 Ph(2,6-Cl₂) Me O O OH III-87 Ph(3,4-Me₂) MeO O OH III-88 Ph(3,5-Me₂) Me O O OH III-89 Ph(2,3-Me₂) Me O O OH III-90Ph(2,4-Me₂) Me O O OH III-91 Ph(2,5-Me₂) Me O O OH III-92 Ph(2,6-Me₂) MeO O OH III-93 Ph(3,4-(OMe)₂) Me O O OH III-94 Ph(3,5-(OMe)₂) Me O O OHIII-95 Ph(2,3-(OMe)₂) Me O O OH III-96 Ph(2,4-(OMe)₂) Me O O OH III-97Ph(2,5-(OMe)₂) Me O O OH III-98 Ph(2,6-(OMe)₂) Me O O OH III-99Ph(3-F-4-OMe) Me O O OH III-100 Ph(3-F-5-OMe) Me O O OH III-101Ph(2-F-3-OMe) Me O O OH III-102 Ph(2-F-4-OMe) Me O O OH III-103Ph(2-F-5-OMe) Me O O OH III-104 Ph(2-F-6-OMe) Me O O OH III-105Ph(3-F-4-Me) Me O O OH III-106 Ph(3-F-5-Me) Me O O OH III-107Ph(2-F-3-Me) Me O O OH III-108 Ph(2-F-4-Me) Me O O OH III-109Ph(2-F-5-Me) Me O O OH III-110 Ph(2-F-6-Me) Me O O OH III-111Ph(3-OMe-4-F) Me O O OH III-112 Ph(2-OMe-3-F) Me O O OH III-113Ph(2-OMe-4-F) Me O O OH III-114 Ph(2-OMe-5-F) Me O O OH III-115Ph(3-Me-4-F) Me O O OH III-116 Ph(2-Me-3-F) Me O O OH III-117Ph(2-Me-4-F) Me O O OH

TABLE 31 Compound No. R¹ R² Y Z R⁴ III-118 Ph(2-Me-5-F) Me O O OHIII-119 Ph(3-Cl-4-OMe) Me O O OH III-120 Ph(3-Cl-5-OMe) Me O O OHIII-121 Ph(2-Cl-3-OMe) Me O O OH III-122 Ph(2-Cl-4-OMe) Me O O OHIII-123 Ph(2-Cl-5-OMe) Me O O OH III-124 Ph(2-Cl-6-OMe) Me O O OHIII-125 Ph(3-Cl-4-Me) Me O O OH III-126 Ph(3-Cl-5-Me) Me O O OH III-127Ph(2-Cl-3-Me) Me O O OH III-128 Ph(2-Cl-4-Me) Me O O OH III-129Ph(2-Cl-5-Me) Me O O OH Ill-130 Ph(2-Cl-6-Me) Me O O OH III-131Ph(3-OMe-4-Cl) Me O O OH III-132 Ph(2-OMe-3-Cl) Me O O OH III-133Ph(2-OMe-4-Cl) Me O O OH III-134 Ph(2-OMe-5-Cl) Me O O OH III-135Ph(3-Me-4-Cl) Me O O OH III-136 Ph(2-Me-3-Cl) Me O O OH III-137Ph(2-Me-4-Cl) Me O O OH III-138 Ph(2-Me-5-Cl) Me O O OH III-139Ph(3-F-4-Cl) Me O O OH III-140 Ph(3-F-5-Cl) Me O O OH III-141Ph(2-F-3-Cl) Me O O OH III-142 Ph(2-F-4-Cl) Me O O OH III-143Ph(2-F-5-Cl) Me O O OH III-144 Ph(2-F-6-Cl) Me O O OH III-145Ph(3-Cl-4-F) Me O O OH III-146 Ph(2-Cl-3-F) Me O O OH III-147Ph(2-Cl-4-F) Me O O OH III-148 Ph(2-Cl-5-F) Me O O OH III-149Ph(3-Me-4-OMe) Me O O OH III-150 Ph(3-Me-5-OMe) Me O O OH III-151Ph(2-Me-3-OMe) Me O O OH III-152 Ph(2-Me-4-OMe) Me O O OH III-153Ph(2-Me-5-OMe) Me O O OH III-154 Ph(2-Me-6-OMe) Me O O OH III-155Ph(3-OMe-4-Me) Me O O OH III-156 Ph(2-OMe-3-Me) Me O O OH

TABLE 32 Compound No. R¹ R² Y Z R⁴ III-157 Ph(2-OMe-4-Me) Me O O OHIII-158 Ph(2-OMe-5-Me) Me O O OH III-159 Ph(3-CN-4-OMe) Me O O OHIII-160 Ph(3-OMe-4-CN) Me O O OH III-161 Ph(3-Me-4-CN) Me O O OH III-162Ph(3-CN-4-Me) Me O O OH III-163 Ph(3-NO₂-4-OMe) Me O O OH III-164Ph(3-OMe-4-NO₂) Me O O OH III-165 Ph(3-Me-4-NO₂) Me O O OH III-166Ph(3-NO₂-4-Me) Me O O OH III-167 Ph(3,5-F₂-5-OMe) Me O O OH III-168Ph(3,5-F₂-5-Me) Me O O OH III-169 Ph(3,4,5-(OMe)₃) Me O O OH III-170

Me O O OH III-171

Me O O OH III-172

Me O O OH III-173

Me O O OH III-174

Me O O OH III-175

Me O O OH III-176

Me O O OH III-177

Me O O OH III-178

Me O O OH

TABLE 33 Compound No. R¹ R² Y Z R⁴ III-179

Me O O OH III-180

Me O O OH III-181

Me O O OH III-182

Me O O OH III-183

Me O O OH III-184

Me O O OH III-185

Me O O OH III-186

Me O O OH III-187

Me O O OH III-188

Me O O OH III-189

Me O O OH III-190

Me O O OH III-191

Me O O OH III-192

Me O O OH

TABLE 34 Compound No. R¹ R² Y Z R⁴ III-193

Me O O OH III-194

Me O O OH III-195

Me O O OH III-196

Me O O OH III-197

Me O O OH III-198

Me O O OH III-199

Me O O OH III-200

Me O O OH III-201

Me O O OH III-202

Me O O OH III-203

Me O O OH III-204

Me O O OH III-205 CH₂Ph Me O O OH III-206 CH₂CH₂Ph Me O O OH III-207CH₂CH₂CH₂Ph Me O O OH III-208 CH₂CH═CHPh Me O O OH III-209 CH₂C≡CPh Me OO OH III-210 CH₂CH═NOMe Me O O OH III-211 CH₂CH═NOEt Me O O OH

TABLE 35 Compound No. R¹ R² Y Z R⁴ III-212 CH₂CH═NOPr-n Me O O OHIII-213 CH₂CH═NOPh Me O O OH III-214 CH₂CH(OMe)₂ Me O O OH III-215CH₂CHO Me O O OH III-216 NH₂ Me O O OH III-217 NHMe Me O O OH III-218NHEt Me O O OH III-219 NHPr-n Me O O OH III-220 NHPr-i Me O O OH III-221NHBu-n Me O O OH III-222 NHBu-i Me O O OH III-223 NHBu-s Me O O OHIII-224 NHCH₂Pr-c Me O O OH III-225 NHPen-n Me O O OH III-226 NHHex-n MeO O OH III-227 NHCH₂CH₂CH₂Cl Me O O OH III-228 NHCH₂CH₂CH₂F Me O O OHIII-229 NHCH₂CH₂OMe Me O O OH III-230 NMe₂ Me O O OH III-231 NEt₂ Me O OOH III-232 N(Pr-n)₂ Me O O OH III-233 N(Bu-n)₂ Me O O OH III-234 N(Me)EtMe O O OH III-235 N(Me)CH₂CH₂OMe Me O O OH III-236 NHPh Me O O OHIII-237 NHCH₂Ph Me O O OH III-238 N═CMe₂ Me O O OH III-239 N═CEt₂ Me O OOH III-240 N═CHNMe₂ Me O O OH III-241 NHC(═O)Me Me O O OH III-242N[C(═O)Me]₂ Me O O OH III-243 NHC(═O)OMe Me O O OH III-244 N[C(═O)OMe]₂Me O O OH III-245 NHSO₂Me Me O O OH III-246 NHSO₂Ph Me O O OH III-247NHSO₂CH₂Ph Me O O OH III-248 OMe Me O O OH III-249 OEt Me O O OH III-250OPr-n Me O O OH III-251 OPr-i Me O O OH III-252 OCH₂Pr-c Me O O OHIII-253 OCH₂Cl Me O O OH III-254 OCHCl₂ Me O O OH

TABLE 36 Compound No. R¹ R² Y Z R⁴ III-255 OCCl₃ Me O O OH III-256 OCH₂FMe O O OH III-257 OCHF₂ Me O O OH III-258 OCF₃ Me O O OH III-259 Ph Et OO OH III-260 Ph Pr-i O O OH III-261 Ph CHF₂ O O OH III-262 Ph Ph O O OHIII-263 Ph Me O S OH III-264 Ph Me S S OH III-265 Me Me O S OH III-266Me Me S S OH III-267 Ph Me O O SPh III-268 Ph(4-OEt) Me O O OH III-269Ph(2-Ph) Me O O OH III-270 Ph(3-Ph) Me O O OH III-271 Ph(4-Ph) Me O O OHIII-272

Me O O OH III-273

Me O O OH III-274 Me

O O OH III-275 Et

O O OH III-276 H Me O O OH III-277 CH₂C≡CF Me O O OH III-278

Me O O OH III-279

Me O O OH III-280 CH₂NH₂ Me O O OH III-281 CH₂NO₂ Me O O OH III-282CH₂NHCH₃ Me O O OH III-283 CH₂N(CH₃)₂ Me O O OH III-284 CH₂SCH₂CF₃ Me OO OH III-285 CH₂SOCH₂CF₃ Me O O OH III-286 CH₂SO₂CH₂CF₃ Me O O OHIII-287 CH₂OH Me O O OH III-288 CH₂OBn Me O O OH III-289 CH₂OCH₂Pr-c MeO O OH

TABLE 37 Compound No. R¹ R² Y Z R⁴ III-290 CH₂OPh Me O O OH III-291CH₂SPh Me O O OH III-292 CH₂SOPh Me O O OH III-293 CH₂SO₂Ph Me O O OHIII-294 CH₂CON(CH₃)₂ Me O O OH III-295 CH₂COCH₃ Me O O OH III-296CH₂OCOCH₃ Me O O OH III-297 CH₂ON═CHCH₃ Me O O OH III-298 C₂H₄OC₂H₄SCH₃Me O O OH III-299 C₂H₄OC₂H₄SOCH₃ Me O O OH III-300 C₂H₄OC₂H₄SO₂CH₃ Me OO OH III-301 CH₂OCH₂CN Me O O OH III-302 CH₂CN Me O O OH III-303OCH₂CH═CH₂ Me O O OH III-304 OCH₂C≡CH Me O O OH III-305 OPr-c Me O O OHIII-306

Me O O OH III-307

Me O O OH III-308

Me O O OH III-309

Me O O OH III-310

Me O O OH III-311 Ph H O O OH III-312 Ph CH₂CH═CH₂ O O OH III-313 PhCH₂C≡CH O O OH III-314 Ph Pr-c O O OH III-315 Ph CH₂CH═CF₂ O O OHIII-316 Ph CH₂C≡CF O O OH III-317 Ph C₂H₄OCH₃ O O OH III-318 PhC₂H₄OC₂H₅ O O OH III-319 Ph CH(Me)OEt O O OH III-320 Ph CH₂OPr-c O O OHIII-321 Ph CH(OCH₃)₂ O O OH III-322 Ph CH₂Ph O O OH III-323 Ph

O O OH

TABLE 38 Com- pound No. R¹ R² Y Z R⁴ III-324 Ph

O O OH III-325 Ph Me O O NH₂ III-326 Ph Me O O Cl III-327 Ph Me O O CNIII-328 Ph Me O O NCS III-329 Ph Me O O NCO III-330 Ph Me O O OCO₂HIII-331 Ph Me O O OCO₂CH₃ III-332 Ph Me O O OCO₂CH₂Ph III-333 Ph Me O OOMe III-334 Ph Me O O OEt III-335 Ph Me O O OPr III-336 Ph Me O OOCH₂CH═CH₂ III-337 Ph Me O O OCH₂C≡CH III-338 Ph Me O O OPr-c III-339 PhMe O O OBu-c III-340 Ph Me O O OPen-c III-341 Ph Me O O OHex-c III-342Ph Me O O OCH₂CN III-343 Ph Me O O OCH₂Pr-c III-344 Ph Me O O OCOCH₃III-345 Ph Me O O OCOCCl₃ III-346 Ph Me O O OCOCH═CH₂ III-347 Ph Me O OOCOCH═CF₂ III-348 Ph Me O O OCOCH₂C≡CH III-349 Ph Me O O OCOCH₂C≡CFIII-350 Ph Me O O OCH₂CO₂CH₃ III-351 Ph Me O O OPh III-352 Ph Me O OOCH₂Ph III-353 Ph Me O O OCOPh III-354 Ph Me O O OCOCH₂Ph III-355 Ph MeO O OCH₂COPh III-356 Ph Me O O OSO₂CH₂CF₃ III-357 Ph Me O O OSO₂CH₂PhIII-358 Ph Me O O SCH₃ III-359 Ph Me O O SOCH₃ III-360 Ph Me O O SO₂CH₃III-361 Ph Me O O SCH₂CF₃ III-362 Ph Me O O SOCH₂CF₃ III-363 Ph Me O OSO₂CH₂CF₃ III-364 Ph Me O O SCH₂CH═CH₂ III-365 Ph Me O O SOCH₂CH═CH₂III-366 Ph Me O O SO₂CH₂CH═CH₂

TABLE 39 Compound No. R¹ R² Y Z R⁴ III-367 Ph Me O O SCH₂CH≡CH III-368Ph Me O O SOCH₂CH≡CH III-369 Ph Me O O SO₂CH₂CH≡CH III-370 Ph Me O OSCH₂Ph III-371 Ph Me O O SOPh III-372 Ph Me O O SOCH₂Ph III-373 Ph Me OO SO₂Ph III-374 Ph Me O O SO₂CH₂Ph III-375 Ph Me O O NHCH₃ III-376 Ph MeO O N(CH₃)₂ III-377 Ph Me O O NHCOCH₃ III-378 Ph Me O O

III-379 Ph Me O O

III-380 Ph Me O O

III-381 Ph Me O O

III-382 Ph Me O O

III-383 Ph Me O O

TABLE 40

Com- pound No. R¹ A₁ A₂ A₃ VI-1  Ph C(CH₃)₂ CO C(CH₃)₂ VI-2  Ph CHCH₃CH₂ CH₂ VI-3  Ph CH₂ CHCH₃ CH₂ VI-4  Ph CHCH₃ CHCH₃ CHCH₃ VI-5  PhC(CH₃)₂ CH₂ CH₂ VI-6  Ph CH₂ C(CH₃)₂ CH₂ VI-7  Ph CHCH₃ CH₂ C(CH₃)₂VI-8  Ph CHCH₃ CH₂ CHCH₃ VI-9  Ph CHCH₃ CHCH₃ CH₂ VI-10 Ph NCH₃ CO CH₂VI-11 Ph C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-12 Ph C(CH₃)₂ S C(CH₃)₂ VI-13 PhC(CH₃)₂ SO C(CH₃)₂ VI-14 Ph C(CH₃)₂ SO₂ C(CH₃)₂ VI-15 Ph C(CH₃)₂ OC(CH₃)₂ VI-16 Ph C(CH₃)₂ NCH₃ C(CH₃)₂ VI-17 Me C(CH₃)₂ CO C(CH₃)₂ VI-18Me CHCH₃ CH₂ CH₂ VI-19 Me CH₂ CHCH₃ CH₂ VI-20 Me CHCH₃ CHCH₃ CHCH₃ VI-21Me C(CH₃)₂ CH₂ CH₂ VI-22 Me CH₂ C(CH₃)₂ CH₂ VI-23 Me CHCH₃ CH₂ C(CH₃)₂VI-24 Me CHCH₃ CH₂ CHCH₃ VI-25 Me CHCH₃ CHCH₃ CH₂ VI-26 Me NCH₃ CO CH₂VI-27 Me C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-28 Me C(CH₃)₂ S C(CH₃)₂ VI-29 MeC(CH₃)₂ SO C(CH₃)₂ VI-30 Me C(CH₃)₂ SO₂ C(CH₃)₂ VI-31 Me C(CH₃)₂ OC(CH₃)₂ VI-32 Me C(CH₃)₂ NCH₃ C(CH₃)₂ VI-33

C(CH₃)₂ CO C(CH₃)₂ VI-34

CHCH₃ CH₂ CH₂

TABLE 41 Com- pound No. R¹ A₁ A₂ A₃ VI-35

CH₂ CHCH₃ CH₂ VI-36

CHCH₃ CHCH₃ CHCH₃ VI-37

C(CH₃)₂ CH₂ CH₂ VI-38

CH₂ C(CH₃)₂ CH₂ VI-39

CHCH₃ CH₂ C(CH₃)₂ VI-40

CHCH₃ CH₂ CHCH₃ VI-41

CHCH₃ CHCH₃ CH₂ VI-42

NCH₃ CO CH₂ VI-43

C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-44

C(CH₃)₂ S C(CH₃)₂ VI-45

C(CH₃)₂ SO C(CH₃)₂ VI-46

C(CH₃)₂ SO₂ C(CH₃)₂ VI-47

C(CH₃)₂ O C(CH₃)₂ VI-48

C(CH₃)₂ NCH₃ C(CH₃)₂ VI-49 Ph(4-OMe) C(CH₃)₂ CO C(CH₃)₂ VI-50 Ph(4-OMe)CHCH₃ CH₂ CH₂ VI-51 Ph(4-OMe) CH₂ CHCH₃ CH₂ VI-52 Ph(4-OMe) CHCH₃ CHCH₃CHCH₃ VI-53 Ph(4-OMe) C(CH₃)₂ CH₂ CH₂ VI-54 Ph(4-OMe) CH₂ C(CH₃)₂ CH₂VI-55 Ph(4-OMe) CHCH₃ CH₂ C(CH₃)₂ VI-56 Ph(4-OMe) CHCH₃ CH₂ CHCH₃ VI-57Ph(4-OMe) CHCH₃ CHCH₃ CH₂

TABLE 42 Compound No. R¹ A₁ A₂ A₃ VI-58 Ph(4-OMe) NCH₃ CO CH₂ VI-59Ph(4-OMe) C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-60 Ph(4-OMe) C(CH₃)₂ S C(CH₃)₂VI-61 Ph(4-OMe) C(CH₃)₂ SO C(CH₃)₂ VI-62 Ph(4-OMe) C(CH₃)₂ SO₂ C(CH₃)₂VI-63 Ph(4-OMe) C(CH₃)₂ O C(CH₃)₂ VI-64 Ph(4-OMe) C(CH₃)₂ NCH₃ C(CH₃)₂VI-65 Ph(2,4-Me₂) C(CH₃)₂ CO C(CH₃)₂ VI-66 Ph(2,4-Me₂) CHCH₃ CH₂ CH₂VI-67 Ph(2,4-Me₂) CH₂ CHCH₃ CH₂ VI-68 Ph(2,4-Me₂) CHCH₃ CHCH₃ CHCH₃VI-69 Ph(2,4-Me₂) C(CH₃)₂ CH₂ CH₂ VI-70 Ph(2,4-Me₂) CH₂ C(CH₃)₂ CH₂VI-71 Ph(2,4-Me₂) CHCH₃ CH₂ C(CH₃)₂ VI-72 Ph(2,4-Me₂) CHCH₃ CH₂ CHCH₃VI-73 Ph(2,4-Me₂) CHCH₃ CHCH₃ CH₂ VI-74 Ph(2,4-Me₂) NCH₃ CO CH₂ VI-75Ph(2,4-Me₂) C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-76 Ph(2,4-Me₂) C(CH₃)₂ S C(CH₃)₂VI-77 Ph(2,4-Me₂) C(CH₃)₂ SO C(CH₃)₂ VI-78 Ph(2,4-Me₂) C(CH₃)₂ SO₂C(CH₃)₂ VI-79 Ph(2,4-Me₂) C(CH₃)₂ O C(CH₃)₂ VI-80 Ph(2,4-Me₂) C(CH₃)₂NCH₃ C(CH₃)₂ VI-81

C(CH₃)₂ CO C(CH₃)₂ VI-82

CHCH₃ CH₂ CH₂ VI-83

CH₂ CHCH₃ CH₂ VI-84

CHCH₃ CHCH₃ CHCH₃ VI-85

C(CH₃)₂ CH₂ CH₂ VI-86

CH₂ C(CH₃)₂ CH₂ VI-87

CHCH₃ CH₂ C(CH₃)₂ VI-88

CHCH₃ CH₂ CHCH₃

TABLE 43 Com- pound No. R¹ A₁ A₂ A₃ VI-89

CHCH₃ CHCH₃ CH₂ VI-90

NCH₃ CO CH₂ VI-91

C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-92

C(CH₃)₂ S C(CH₃)₂ VI-93

C(CH₃)₂ SO C(CH₃)₂ VI-94

C(CH₃)₂ SO₂ C(CH₃)₂ VI-95

C(CH₃)₂ O C(CH₃)₂ VI-96

C(CH₃)₂ NCH₃ C(CH₃)₂ VI-97 Ph(3,4,5-(OMe)₃) C(CH₃)₂ CO C(CH₃)₂

Preferred examples of the triazine derivative represented by Formula 1of the invention or salt thereof include the followings.

A in Formula 1 is preferably A-1, A-3, or A-5, and more preferably A-1or A-3.

In A-1, A₁ is preferably [X₁], A₂ is preferably [X₃] or [X₄], and A₃ ispreferably [X₉].

In [X₁], R⁵ and R⁶ are preferably a hydrogen atom or a C₁-C₆ alkylgroup. In [X₃], R¹ and R⁹ are preferably a hydrogen atom or a C₁-C₆alkyl group. In [X₉], R³⁵ and R³⁶ are preferably a hydrogen atom or aC₁-C₆ alkyl group. Further, according to the preferred example of theinvention, R⁵ in [X₁] and R³⁵ in [X₉] bind to each other via a C₁-C₅alkylene chain, preferably an ethylene chain, to form a ring.

In A-3, R²⁰ is preferably a C₁-C₆ alkyl group and R²¹ is preferably ahydrogen atom or a C₁-C₆ alkyl group.

In A-1 and A-3, R¹ is preferably a hydroxyl group, an O⁻M⁺ (M⁺represents an alkali metal cation or an ammonium cation), or a C₁-C₁₀alkylsulfonyloxy group.

In Formula 1, Y is preferably an oxygen atom.

In Formula 1, R¹ is preferably a group selected from a group consistingof a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; aC₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkylgroup; a C₂-C₆ halolalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; aC₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkylgroup; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonylC₁-C₆ alkyl group; a phenyl group which may be substituted with asubstituent group selected from Substituent group α; a phenyl C₁-C₆alkyl group which may be substituted with a substituent group selectedfrom Substituent group α; and a heterocyclic group having 3 to 10 carbonatoms and one or more heteroatoms that are the same or different fromeach other and selected from an oxygen atom, a sulfur atom, and anitrogen atom (the group may be substituted with one substituent groupselected from Substituent group α or 2 to 5 substituent groups that arethe same or different from each other and selected from Substituentgroup α, and when the heterocyclic group contains a sulfur atom, it maybe oxidized to be present as sulfoxide or sulfone).

In Formula 1, R² is preferably a group selected from a group consistingof a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group whichmay be substituted with a substituent group selected from Substituentgroup α; and a heterocyclic group having 3 to 10 carbon atoms and one ormore heteroatoms that are the same or different from each other andselected from an oxygen atom, a sulfur atom, and a nitrogen atom (thegroup may be substituted with one substituent group selected fromSubstituent group α or 2 to 5 substituent groups that are the same ordifferent from each other and selected from Substituent group α).

The triazine derivative compounds represented by Formula 1, i.e., thecompounds of the invention, and their salts can be produced according tovarious methods. Representative examples of the production method aregiven below, but the invention is not limited to them.

<Production Method 1>

The compound represented by following Formula 1a, which is one of thecompounds of the invention, can be produced according to the method withthe reaction scheme shown below.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z have the same definitionsas above and Q represents a leaving group like a halogen atom, analkylcarbonyloxy group, an alkoxycarbonyloxy group, ahaloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxygroup, a pyridyl group, and an imidazolyl group).

(Process 1)

By reacting the compound of Formula 3 and the compound of Formula 4a ina solvent in the presence of a base, the enolester compound of Formula5a and/or Formula 5b can be produced.

Herein, the use amount of Formula 4a can be appropriately selected fromthe range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it isfrom 1.0 to 1.2 mol.

Examples of the base which can be used for the present process includeorganic amines like triethylamine, pyridine, 4-dimethylaminopyridine,N,N-dimethylaniline, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU); metalcarbonates like sodium carbonate, potassium carbonate, magnesiumcarbonate, and calcium carbonate; metal hydrogen carbonates like sodiumhydrogen carbonate and potassium hydrogen carbonate; metal carboxylatesalts represented by metal acetate salts like sodium acetate, potassiumacetate, calcium acetate, and magnesium acetate; metal alkoxides likesodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassiummethoxide, and potassium tertiary butoxide; metal hydroxides like sodiumhydroxide, potassium hydroxide, calcium hydroxide, and magnesiumhydroxide, and; metal hydrides like lithium hydride, sodium hydride,potassium hydride, and calcium hydride. The use amount of the base isappropriately selected from the range of 0.5 to 10 mol per 1 mol ofFormula 3. Preferably, it is from 1.0 to 1.2 mol.

The solvent that can be used for the present process can be any solventif it does not inhibit the progress of the reaction. Solvents includingnitriles like acetonitrile; ethers like diethyl ether, diisopropylether, tetrahydrofuran, dioxane, monoglyme, and diglyme; halogenatedhydrocarbons like dichloroethane, chloroform, carbon tetrachloride, andtetrachloroethane; aromatic hydrocarbons like benzene, chlorobenzene,nitrobenzene, and toluene; amides like N,N-dimethylformamide andN,N-dimethylacetamide; imidazolinones like 1,3-dimethyl-2-imidazolinone,and; sulfur compounds like dimethyl sulfoxide can be used. Further,their mixture solvent can be also used.

The reaction temperature may be selected from the range of from −20° C.to the boiling point of an inert solvent used. Preferably, the reactionis carried out in the range of from 0° C. to 100° C. By using a phasetransfer catalyst like quaternary ammonium salt, the reaction can becarried out in a two-phase system.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 5a and/orFormula 5b, which is the target compound of the reaction, can becollected from the reaction system by general method, and if necessary,purified by a process like column chromatography and recrystallization.

(Process 2)

Compound of Formula 5a and/or Formula 5b can be also produced byreacting the compound of Formula 3 and the compound of Formula 4b with adehydrating condensing agent in a solvent, in the presence or absence ofa base.

The use amount of Formula 4b that is used for the present process can beappropriately selected from the range of 0.5 to 10 mol per 1 mol ofFormula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the dehydrating condensing agent include dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N′-ehtylcarbodiimide (EDCor WSC), N,N-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazoliumchloride, and 2-chloro-1-pyridinium iodide.

Examples of the base and the solvent which can be used for the presentprocess include those described above for Process 1.

The reaction temperature may be selected from the range of from −20° C.to the boiling point of an inert solvent used. Preferably, the reactionis carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

The compound of Formula 5a and/or Formula 5b, which is the targetcompound of the reaction, can be separated and purified in the samemanner as Process 1.

(Process 3)

Compound of Formula 1a can be produced by reacting the compound ofFormula 5a and/or Formula 5b produced by Process 1 or Process 2 with acyano compound in the presence of a base.

Examples of the base which can be used for the present process includethose described above for Process 1. The use amount of the base can beappropriately selected from the range of 0.5 to 10 mol per 1 mol ofFormula 5a and Formula 5b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the cyano compound which can be used for the present processinclude potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogencyanide, and a polymer supported with hydrogen cyanide. The use amountof the cyano compound can be appropriately selected from the range of0.01 to 1.0 mol per 1 mol of Formula 5a and Formula 5b. Preferably, itis from 0.05 to 0.2 mol.

For the present process, a small amount of a phase transfer catalystlike crown ether can be also used.

Examples of the solvent which can be used for the present processinclude those described above for Process 1. The reaction temperature isselected from the range of from −20° C. to the boiling point of an inertsolvent used. Preferably, the reaction is carried out in the range offrom 0° C. to 100° C. The reaction time varies depending on the reactiontemperature, the reaction substrates, the reaction amount, etc. Ingeneral, it is from 10 minutes to 48 hours.

Further, according to the present process, compound of Formula 1a can beproduced while using Formula 5a and/or Formula 5b produced by Process 1or Process 2 without any separation.

(Process 4)

Compound of Formula 1a can be also produced by reacting the compound ofFormula 3 and the compound of Formula 4c in the presence of a base or aLewis acid.

The use amount of Formula 4c that is used for the present process can beappropriately selected from the range of 0.5 to 10 mol per 1 mol ofFormula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the Lewis acid include zinc chloride and aluminum chloride.

Examples of the base which can be used for the present process includethose described above for Process 1. The use amount of the base that canbe used for the present process can be appropriately selected from therange of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, compound of Formula 1a, which isproduced according to Process 3 or Process 4, can be collected from thereaction system by general method, and if necessary, purified by aprocess like column chromatography and recrystallization.

<Production Method 2>

With regard to Formula 1a produced by Production method 1, the hydroxylgroup in the cyclohexane ring can be converted to other substituentgroup according to the method with the following reaction scheme.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z each have the samedefinitions as above, R^(4a) represents an amino group, a cyano group,an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxygroup, a C₁-C₆ alkoxycarbonyloxy group, a benzyloxycarbonyloxy groupwhich may be substituted with a substituent group selected fromSubstituent group α, a C₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, aC₂-C₆ alkynyloxy group, a C₃-C₆ cycloalkyloxy group, a cyanomethyleneoxygroup, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ alkylcarbonyloxygroup, a C₁-C₆ haloalkylcarbonyloxy group, a C₂-C₆ alkenylcarbonyloxygroup, a C₂-C₆ halolalkcnylcarbonyloxy group, a C₂-C₆ alkynylcarbonyloxygroup, a C₂-C₆ halolalkynylcarbonyloxy group, a C₁-C₆ alkoxycarbonylC₁-C₆ alkoxy group, a phenyloxy group which may be substituted with asubstituent group selected from Substituent group α, a benzyloxy groupwhich may be substituted with a substituent group selected fromSubstituent group α, a phenylcarbonyloxy group which may be substitutedwith a substituent group selected from Substituent group α, abenzylcarbonyloxy group which may be substituted with a substituentgroup selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyloxygroup which may be substituted with a substituent group selected fromSubstituent group α, a C₁-C₁₀ alkylsulfonyloxy group, aphenylsulfonyloxy group which may be substituted with a substituentgroup selected from Substituent group α, a benzylsulfonyloxy group whichmay be substituted with a substituent group selected from Substituentgroup α, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinyl group, aC₁-C₁₀ alkylsulfonyl group, a C₁-C₆ haloalkylthio group, a C₁-C₆haloalkylsulfinyl group, a C₁-C₆ haloalkylsulfonyl group, a C₂-C₆alkenylthio group, a C₂-C₆ alkenylsulfinyl group, a C₂-C₆alkenylsulfonyl group, a C₂-C₆ alkynylthio group, a C₂-C₆alkynylsulfinyl group, a C₂-C₆ alkynylsulfonyl group, a phenylthio groupwhich may be substituted with a substituent group selected fromSubstituent group α, a benzylthio group which may be substituted with asubstituent group selected from Substituent group α, a phenylsulfinylgroup which may be substituted with a substituent group selected fromSubstituent group α, a benzylsulfinyl group which may be substitutedwith a substituent group selected from Substituent group α, aphenylsulfonyl group which may be substituted with a substituent groupselected from Substituent group α, a benzylsulfonyl group which may besubstituted with a substituent group selected from Substituent group α,a C₁-C₁₀ alkylamino group, a di(C₁-C₁₀ alkyl)amino group, a C₁-C₆alkoxycarbonyl amino group, a C₁-C₆ alkoxy group substituted with aheterocyclic group having 3 to 10 carbon atoms and one or moreheteroatoms that are the same or different from each other and selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom [the group maybe substituted with one substituent group selected from Substituentgroup α or 2 to 5 substituent groups that are the same or different fromeach other and selected from Substituent group α], a heterocyclic grouphaving 3 to 10 carbon atoms and one or more heteroatoms that are thesame or different from each other and selected from an oxygen atom, asulfur atom, and a nitrogen atom [the group may be substituted with onesubstituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α], or a heterocyclic oxy group having 3to 10 carbon atoms and one or more heteroatoms that are the same ordifferent from each other and selected from an oxygen atom, a sulfuratom, and a nitrogen atom [the group may be substituted with onesubstituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α], and X represents a halogen atom).

Specifically, the compound of Formula 1b can be produced by reacting thecompound of Formula 1a and a halogenating agent, and Formula 1c can beproduced by reacting the compound of Formula 1b and a nucleophilicreagent in the presence of a base.

Examples of the halogenating agent that can be used for preparation ofthe compound of Formula 1b from the compound of Formula 1a includethionyl chloride, thionyl bromide, phosphorus oxy chloride, phosphorusoxy bromide, phenyltrimethyl ammonium tribromide, and Meldrum's acidtribromide. The use amount of the halogenating agent can beappropriately selected from the range of 0.5 to 10 mol per 1 mol ofFormula 1a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.

The reaction temperature may be selected from the range of from −20° C.to the boiling point of an inert solvent used. Preferably, the reactionis carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

Examples of the nucleophilic reagent for the process for obtainingFormula 1c from Formula 1b, which is a compound represented by theformula R^(4a)—H, include alcohols like methanol, ethanol, and benzylalcohol; mercaptans like methyl mercaptan and ethyl mercaptan; amineslike ammonia, methyl amine, and ethyl amine; phenols like p-cresol andphenol; thiophenols like p-chlorothiophenol; a C₁-C₆ alkyl acids likeacetic acid, and benzoic acids. The use amount of the nucleophilicreagent can be appropriately selected from the range of 0.5 to 10 molper 1 mol of Formula 1b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process includethose described above for Process 1 of Production method 1.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1c, whichis produced according to this method, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

<Production Method 3>

Compound of Formula 1c can be also produced by the method with thefollowing reaction scheme.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z each have the samedefinitions as above, R^(4a) represents a hydroxycarbonyl group, a C₁-C₆alkoxycarbonyl group, a benzyloxycarbonyl group which may be substitutedwith a substituent group selected from Substituent group c, a C₁-C₆alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a C₃-C₆cycloalkyl group, a cyanomethylene group, a C₃-C₆ cycloalkyl C₁-C₆ alkylgroup, a C₁-C₆ alkylcarbonyl group, a C₁-C₁₀ alkylthiocarbonyl group, aC₁-C₆ haloalkylcarbonyl group, a C₂-C₆ alkenylcarbonyl group, a C₂-C₆halolalkenylcarbonyl group, a C₂-C₆ alkynylcarbonyl group, a C₂-C₆halolalkynylcarbonyl group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group, aC₁-C₁₀ alkylsulfonyl group, a phenyl group which may be substituted witha substituent group selected from Substituent group α, a benzyl groupwhich may be substituted with a substituent group selected fromSubstituent group α, a phenylcarbonyl group which may be substitutedwith a substituent group selected from Substituent group α, abenzylcarbonyl group which may be substituted with a substituent groupselected from Substituent group α, a phenylsulfonyl group which may besubstituted with a substituent group selected from Substituent group α,a phenylcarbonyl C₁-C₆ alkyl group which may be substituted with asubstituent group selected from Substituent group α, or a heterocyclicgroup having 3 to 10 carbon atoms and one or more heteroatoms that arethe same or different from each other and selected from an oxygen atom,a sulfur atom, and a nitrogen atom [the group may be substituted withone substituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α]).

Specifically, the compound of Formula 1c can be produced by reacting thecompound of Formula 1a and an electrophilic reagent in a solvent in thepresence or absence of a base.

The electrophilic reagent indicates a compound represented by theformula R^(4b)-L_(a) (L_(a) represents a leaving group), and examplesthereof include C₁-C₆ alkyl halide like methyl iodide and propylchloride; benzyl halide like benzyl bromide; C₁-C₆ alkylcarbonyl halidelike acetyl chloride and propionyl chloride; benzoyl halide like benzoylchloride; C₂-C₆ alkenylcarbonyl halide like methacryl chloride andcrotonyl chloride; C₂-C₆ alkynylcarbonyl halide like 4-pentynylchloride; C₁-C₆ alkyl sulfonyl halide like methane sulfonyl chloride andethane sulfonyl chloride; benzene sulfonyl halide like benzene sulfonylchloride and p-toluene sulfonyl chloride; and di C₁-C₆ alkyl sulfateester like dimethyl sulfate and diethyl sulfate. The use amount of theelectrophilic reagent can be appropriately selected from the range of0.1 to 10 mol per 1 mol of Formula 1a. Preferably, it is from 1.0 to 1.2mol.

Examples of the base which can be used for the present process includethose described above for Process 1 of Production method 1. The useamount of the base can be appropriately selected from the range of 0.1to 10 mol per 1 mol of Formula 1a. Preferably, it is from 1.0 to 12 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1c, whichis a target compound of this process, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Formula 1c of the invention has many tautomers shown below, and they areall included in the invention.

<Production Method 4>

Compound of Formula 1d can be also produced by the method with thefollowing reaction scheme.

(in the formula, R¹, R², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, Y and Z each have thesame definitions as above and Q represents a leaving group like ahalogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, ahaloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxygroup, a pyridyl group, and an imidazolyl group, as described above).

Specifically, compound of Formula 1d can be produced by reacting thecompound of Formula 6a and the compound of Formula 4a in a solvent, inthe presence of a Lewis acid.

The use amount of Formula 4a can be appropriately selected from therange of 0.5 to 10 mol per 1 mol of Formula 6a. Preferably, it is from1.0 to 1.2 mol.

Examples of the Lewis acid that can be used include organo lithiumcompounds like methyl lithium, ethyl lithium, n-butyl lithium, sec-butyllithium, tert-butyl lithium, and benzyl lithium; Grignard's reagent likemethyl magnesium iodide and ethyl magnesium bromide; metal compoundslike lithium, potassium and sodium; organo copper compounds producedfrom Grignard's reagent or organometallic compound and monovalent coppersalt; alkali metal amides like lithium diisopropyl amide (LDA), and;organic amines like triethylamine, pyridine, 4-dimethylaminopyridine,N,N-dimethylaniline, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).n-Butyl lithium and lithium diisopropyl amide (LDA) are particularlypreferable. The use amount of Lewis acid can be appropriately selectedfrom the range of 0.5 to 10 mol per 1 mol of Formula 5a. Preferably, itis from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.Diethyl ether and tetrahydrofuran are particularly preferable. Thereaction temperature is selected from the range of from −20° C. to theboiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1d, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Formula 1d of the invention has many tautomers shown below, and they areall included in the invention.

<Production Method 5>

Compound of Formula 1e can be also produced by the method with thefollowing reaction scheme.

(in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the samedefinitions as above and Q represents a leaving group like a halogenatom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, ahaloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxygroup, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5c can be produced by reacting thecompound of Formula 6 and the compound of Formula 4a in a solvent in thepresence of a base, and the compound of Formula 1c can be produced byreacting the compound of Formula 5c and a cyano compound in the presenceof a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5cfrom Formula 6 can be appropriately selected from the range of 0.1 to 10mol per 1 mol of Formula 6. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base and solvent that can be used include thosedescribed above for Process 1 of Production method 1. The reactiontemperature is selected from the range of from −20° C. to the boilingpoint of an inert solvent used. Preferably, the reaction is carried outin the range of from 0° C. to 100° C. The reaction time varies dependingon the reaction temperature, the reaction substrates, the reactionamount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the cyano compound which can be used for the reaction abovefor obtaining Formula 1e from Formula 5c include potassium cyanide,sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymersupported with hydrogen cyanide. The use amount of the cyano compoundcan be appropriately selected from the range of 0.01 to 1.0 mol per 1mol of Formula 6. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above forProcess 1 of Production method 1. The use amount of the base can beappropriately selected from the range of 0.1 to 1.0 mol per 1 mol ofFormula 6. Preferably, it is 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1e, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Formula 1e of the invention has many tautomers shown below, and they areall included in the invention.

<Production Method 6>

Compound of Formula 1g in which the substituent group in the pyrazolering is modified can be also produced from the compound of Formula 1e bythe method with the following reaction scheme.

(in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the samedefinitions as above, R^(22a) represents an amino group, a cyano group,an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxygroup, a C₁-C₆ alkoxycarbonyloxy group, a benzyloxycarbonyloxy groupwhich may be substituted with a substituent group selected fromSubstituent group α, a C₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, aC₂-C₆ alkynyloxy group, a C₃-C₆ cycloalkyloxy group, a cyanomethyleneoxygroup, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ alkylcarbonyloxygroup, a C₁-C₆ haloalkylcarbonyloxy group, a C₂-C₆ alkenylcarbonyloxygroup, a C₂-C₆ halolalkenylcarbonyloxy group, a C₂-C₆ alkynylcarbonyloxygroup, a C₂-C₆ halolalkynylcarbonyloxy group, a C₁-C₆ alkoxycarbonylC₁-C₆ alkoxy group, a phenyloxy group which may be substituted with asubstituent group selected from Substituent group α, a benzyloxy groupwhich may be substituted with a substituent group selected fromSubstituent group α, a phenylcarbonyloxy group which may be substitutedwith a substituent group selected from Substituent group α, abenzylcarbonyloxy group which may be substituted with a substituentgroup selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyloxygroup which may be substituted with a substituent group selected fromSubstituent group α, a C₁-C₁₀ alkylsulfonyloxy group, aphenylsulfonyloxy group which may be substituted with a substituentgroup selected from Substituent group α, a benzylsulfonyloxy group whichmay be substituted with a substituent group selected from Substituentgroup α, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinyl group, aC₁-C₁₀ alkylsulfonyl group, a C₁-C₆ haloalkylthio group, a C₁-C₆haloalkylsulfinyl group, a C₁-C₆ haloalkylsulfonyl group, a C₂-C₆alkenylthio group, a C₂-C₆ alkenylsulfinyl group, a C₂-C₆alkenylsulfonyl group, a C₂-C₆ alkynylthio group, a C₂-C₆alkynylsulfinyl group, a C₂-C₆ alkynylsulfonyl group, a phenylthio groupwhich may be substituted with a substituent group selected fromSubstituent group α, a benzylthio group which may be substituted with asubstituent group selected from Substituent group α, a phenylsulfinylgroup which may be substituted with a substituent group selected fromSubstituent group α, a benzylsulfinyl group which may be substitutedwith a substituent group selected from Substituent group α, aphenylsulfonyl group which may be substituted with a substituent groupselected from Substituent group α, a benzylsulfonyl group which may besubstituted with a substituent group selected from Substituent group α,a C₁-C₁₀ alkylamino group, a di(C₁-C₁₀ alkyl)amino group, a C₁-C₆alkoxycarbonyl amino group, a C₁-C₆ alkoxy group substituted with aheterocyclic group having 3 to 10 carbon atoms and one or moreheteroatoms that are the same or different from each other and selectedfrom an oxygen atom, a sulfur atom, and a nitrogen atom [the group maybe substituted with one substituent group selected from Substituentgroup α or 2 to 5 substituent groups that are the same or different fromeach other and selected from Substituent group α], a heterocyclic grouphaving 3 to 10 carbon atoms and one or more heteroatoms that are thesame or different from each other and selected from an oxygen atom, asulfur atom, and a nitrogen atom [the group may be substituted with onesubstituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α], or a heterocyclic oxy group having 3to 10 carbon atoms and one or more heteroatoms that are the same ordifferent from each other and selected from an oxygen atom, a sulfuratom, and a nitrogen atom [the group may be substituted with onesubstituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α], and X represents a halogen atom).

Specifically, the compound of Formula 1f can be produced by reacting thecompound of Formula 1e and a halogenating agent and Formula 1g can beproduced by reacting it with a nucleophilic reagent.

Examples of the halogenating agent that can be used for the process ofproducing the compound of Formula 1f from the compound of Formula 1einclude thionyl chloride, thionyl bromide, phosphorus oxychloride,phosphorus oxybromide, phenyltrimethyl ammonium tribromide, andMeldrum's acid tribromide.

The use amount of the halogenating agent can be appropriately selectedfrom the range of 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, itis from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1. Thereaction temperature is selected from the range of from −20° C. to theboiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

The nucleophilic reagent for the process for obtaining Formula 1g fromFormula 1f is, for example, a compound represented by the formulaR^(22a)—H, and examples thereof include alcohols like methanol, ethanol,and benzyl alcohol; mercaptans like methyl mercaptan and ethylmercaptan; amines like ammonia, methyl amine, and ethyl amine; phenolslike p-cresol and phenol; thiophenols like p-chlorothiophenol; C₁-C₆alkyl acids like acetic acid, and benzoic acids. The use amount of thenucleophilic reagent can be appropriately selected from the range of 0.1to 10 mol per 1 mol of Formula 1f Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present processinclude those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1g, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

<Production Method 7>

Compound of Formula 1g can be also produced by the method with thefollowing reaction scheme.

(in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the samedefinitions as above, R^(22b) represents a hydroxycarbonyl group, aC₁-C₆ alkoxycarbonyl group, a benzyloxycarbonyl group which may besubstituted with a substituent group selected from Substituent group α,a C₁-C₆ alkyl group, a C2-C6 alkenyl group, a C₂-C₆ alkynyl group, aC₃-C₆ cycloalkyl group, a cyanomethylene group, a C₃-C₆ cycloalkyl C₁-C₆alkyl group, a C₁-C₆ alkylcarbonyl group, a C₁-C₁₀ alkylthiocarbonylgroup, a C₁-C₆ haloalkylcarbonyl group, a C₂-C₆ alkenylcarbonyl group, aC₂-C₆ halolalkenylcarbonyl group, a C₂-C₆ alkynylcarbonyl group, a C₂-C₆halolalkynylcarbonyl group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group, aC₁-C₁₀ alkylsulfonyl group, a phenyl group which may be substituted witha substituent group selected from Substituent group α, a benzyl groupwhich may be substituted with a substituent group selected fromSubstituent group α, a phenylcarbonyl group which may be substitutedwith a substituent group selected from Substituent group α, abenzylcarbonyl group which may be substituted with a substituent groupselected from Substituent group α, a phenylsulfonyl group which may besubstituted with a substituent group selected from Substituent group α,a phenylcarbonyl C₁-C₆ alkyl group which may be substituted with asubstituent group selected from Substituent group α, or a heterocyclicgroup having 3 to 10 carbon atoms and one or more heteroatoms that arethe same or different from each other and selected from an oxygen atom,a sulfur atom, and a nitrogen atom [the group may be substituted withone substituent group selected from Substituent group α or 2 to 5substituent groups that are the same or different from each other andselected from Substituent group α]).

Specifically, the compound of Formula 1g can be produced by reacting thecompound of Formula 1e and an electrophilic reagent in a solvent, in thepresence or absence of a base.

The electrophilic reagent that can be used indicates a compoundrepresented by the formula R^(22b)-L_(a) (L_(a) represents a leavinggroup), and examples thereof include C₁-C₆ alkyl halide like methyliodide and propyl chloride; benzyl halide like benzyl bromide; C₁-C₆alkylcarbonyl halide like acetyl chloride and propionyl chloride; benzylhalide like benzoyl chloride; C₂-C₆ alkenylcarbonyl halide likemethacryl chloride and crotonyl chloride; C₂-C₆ alkynylcarbonyl halidelike 4-pentinoyl chloride; C₁-C₆ alkyl sulfonyl halide methane sulfonylchloride and ethane sulfonyl chloride; benzene sulfonyl halide likebenzene sulfonyl chloride and p-toluene sulfonyl chloride; and di C₁-C₆alkyl sulfate ester like dimethyl sulfate and diethyl sulfate. The useamount of the electrophilic reagent can be appropriately selected fromthe range of 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, it isfrom 1.0 to 1.2 mol.

Examples of the base and the solvent which can be used for the presentprocess include those described above for Process 1 of Production method1.

The use amount of the base can be appropriately selected from the rangeof 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, it is from 1.0 to1.2 mol.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1g, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

<Production Method 8>

Compound of Formula 1h can be also produced by the method with thefollowing reaction scheme.

(in the formula, R¹, R², R²⁴, R²⁵, Y and Z each have the samedefinitions as above and Q represents a leaving group like a halogenatom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, ahaloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxygroup, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5d can be produced by reacting thecompound of Formula 7 and the compound of Formula 4a in a solvent, inthe presence of a base, and the compound of Formula 1h can be producedby reacting the compound of Formula 5d and a cyano compound in thepresence of a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5dfrom Formula 7 can be appropriately selected from the range of 0.1 to 10mol per 1 mol of Formula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used include those described above forProcess 1 of Production method 1. Use amount of the base can beappropriately selected from the range of 0.1 to 10 mol per 1 mol ofFormula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described abovefor Process 1 of Production method 1.

Examples of the cyano compound which can be used for the reaction abovefor obtaining Formula 1h from Formula 5d include potassium cyanide,sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymersupported with hydrogen cyanide. The use amount of the cyano compoundcan be appropriately selected from the range of 0.01 to 1.0 mol per 1mol of Formula 5d. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above forProcess 1 of Production method 1. The use amount of the base can beappropriately selected from the range of 0.1 to 1.0 mol per 1 mol ofFormula 5d. Preferably, it is 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described abovefor Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1h, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Formula 1h of the invention has many tautomers shown below, and they areall included in the invention.

<Production Method 9>

Compound of Formula 1i can be produced by the method with the followingreaction scheme.

(in the formula, R¹, R², R²⁴, Y and Z each have the same definitions asabove, R²⁵ represents a C₁-C₆ alkoxycarbonyl group, R²⁶ represents analkoxy group, a haloalkoxy group, a cycloalkoxy group, or adimethylamino group, and R²⁷ represents an alkyl group or a benzylgroup).

(Process 1)

In this process, Formula 8a can be prepared by reacting Formula 1h andacid with or without using a solvent.

Examples of the acid that can be used for the present process includesulfonic acids like p-toluene sulfonic acid. Use amount of the acid canbe appropriately selected from the range of 0.1 to 10 mol per 1 mol ofFormula 1h. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described abovefor Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 2)

By reacting Formula 8a and an ortho formic acid ester compound inN,N-dimethylacetamide dimethyl acetal compound or acetic anhydride,Formula 8b can be obtained. Use amount of N,N-dimethylacetamide dimethylacetal and ortho formic acid ester can be appropriately selected fromthe range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it isfrom 1.0 to 3.0 mol.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 150° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 3)

Formula 8c can be obtained by reacting Formula 8a and carbon disulfide,and without isolation, adding with alkyl halide like methyl iodide orbenzyl halide like benzyl bromide. Use amount of carbon disulfide can beappropriately selected from the range of 0.1 to 10 mol per 1 mol ofFormula 8a. Preferably, it is from 1.0 to 1.2 mol. Use amount of thehalide can be appropriately selected from the range of 0.1 to 10 mol per1 mol of Formula 8a. Preferably, it is 2.0 to 2.4 mol. Examples of thesolvent that can be used for the present process include those describedabove for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 4 & Process 5)

Formula 1i can be obtained by reacting Formula 8b or Formula 5c obtainedfrom Process 2 or Process 3 above and hydroxylamine chloride in asolvent.

Use amount of hydroxylamine chloride can be appropriately selected fromthe range of 0.1 to 10 mol per 1 mol of Formula 8b or Formula 8c.Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1i, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Hereinbelow, a method of producing synthetic intermediates of thecompounds of the invention is given.

<Production Method 10>

Compound of Formula 3b can be produced by the method with the followingreaction scheme.

(in the formula, R¹, R², Y and Z each have the same definitions asabove, R³⁰ represents a phenyl group or an alkyl group, and M¹represents sodium, potassium or trimethylsilyl).

(Route a)

Specifically, compound of Formula 10 can be obtained by reacting thecompound of Formula 9 and diethyl ketomalonate. In addition, compound ofFormula 13a can be obtained by reacting the compound of Formula 10 andthe compound of Formula 11 or the compound of Formula 12 in the presenceof a base.

Use amount of diethyl ketomalonate for the process of producing Formula10 from Formula 9 can be appropriately selected from the range of 1.0 to1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the compound of Formula 11 or the compound of Formula 12for the process of producing Formula 13a from Formula 10 can beappropriately selected from the range of 1.0 to 1.5 mol per 1 mol ofFormula 10. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used for the present process includethose described above for Process 1 of Production method 1. Use amountof the base can be appropriately selected from the range of 0.1 to 10mol per 1 mol of Formula 10. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

(Route b)

Specifically, compound of Formula 15 can be obtained by reacting thecompound of Formula 9 and the compound of Formula 14. In addition,compound of Formula 16 can be obtained by reacting the compound ofFormula 15 and diethyl ketomalonate. In addition, compound of Formula13a can be obtained by reacting the compound of Formula 16 and analkylating agent in the presence of a base.

Use amount of the compound of Formula 14 for the process of producingFormula 15 from Formula 9 can be appropriately selected from the rangeof 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to12 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula16 from Formula 15 can be appropriately selected from the range of 1.0to 1.5 mol per 1 mol of Formula 15. Preferably, it is from 1.0 to 1.2mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the alkylating agent for the process of producing Formula13a from Formula 16 can be appropriately selected from the range of 1.0to 3.0 mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.5mol.

Examples of the alkylating agent that can be used include alkyl sulfateslike dimethyl sulfate and diethyl sulfate; alkyl halides like methyliodide, ethyl iodide, benzyl chloride, benzyl bromide, propargylbromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acidesters like ethoxyethyl p-toluene sulfonate and cyclopentylmethanesulfonate.

Examples of the base that can be used for the present process includethose described above for Process 1 of Production method 1. Use amountof the base can be appropriately selected from the range of 0.1 to 10mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route c)

Specifically, compound of Formula 17a can be obtained by reacting thecompound of Formula 11a and hydrazine hydrate. In addition, compound ofFormula 18 can be obtained by reacting the compound of Formula 17 anddiethyl ketomalonate. In addition, compound of Formula 13a can beobtained by reacting the compound of Formula 18 and an alkylating agentin the presence of a base.

Use amount of hydrazine hydrate for the process of producing Formula 17afrom Formula 11a can be appropriately selected from the range of 1.0 to1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula18 from Formula 17a can be appropriately selected from the range of 1.0to 1.5 mol per 1 mol of Formula 17a. Preferably, it is from 1.0 to 1.2mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the alkylating agent for the process of producing Formula13a from Formula 18 can be appropriately selected from the range of 1.0to 3.0 mol per 1 mol of Formula 18. Preferably, it is from 1.0 to 1.5mol.

Examples of the alkylating agent that can be used include alkyl sulfateslike dimethyl sulfate and diethyl sulfate; alkyl halides like methyliodide, ethyl iodide, benzyl chloride, benzyl bromide, propargylbromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acidesters like ethoxyethyl p-toluene sulfonate and cyclopentylmethanesulfonate.

Examples of the base that can be used for the present process includethose described above for Process 1 of Production method 1. Use amountof the base can be appropriately selected from the range of 0.1 to 10mol per 1 mol of Formula 18. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, thereaction substrates, the reaction amount, etc. In general, it is from 10minutes to 48 hours.

(Route d)

Specifically, compound of Formula 17b can be obtained by reacting thecompound of Formula 11a and the compound of Formula 9. In addition,compound of Formula 13a can be obtained by reacting the compound ofFormula 17b and diethyl ketomalonate, using an acid or a base dependingon the condition.

Use amount of the compound of Formula 9 for the process of producingFormula 17b from Formula 1a can be appropriately selected from the rangeof 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to1.2 mol.

Examples of the acid that can be used include organic acids representedby organic sulfonic acid like p-toluene sulfonic acid, methane sulfonicacid, and benzene sulfonic acid; hydrogen halide acids represented byhydrochloric acid and hydrogen bromic acid, and; inorganic acids likesulfuric acid and phosphoric acid. These acids can be used either singlyor in combination of two or more.

Examples of the base that can be used for the present process includethose described above for Process 1 of Production method 1.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula13a from Formula 17b can be appropriately selected from the range of 1.0to 1.5 mol per 1 mol of Formula 17b. Preferably, it is from 1.0 to 1.2mol.

Examples of the solvent that can be used for the present process includethose described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the acid include organic acids like p-toluene sulfonic acid.

Examples of the base include organic bases like triethylamine and1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and inorganic bases like sodiumhydride, sodium methoxide, and sodium ethoxide.

After the completion of the reaction, the compound of Formula 13a, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

(Route c)

Specifically, compound of Formula 3b can be obtained by hydrolyzing thecompound of Formula 13a.

With regard to the process of obtaining the compound of Formula 3b fromthe compound of Formula 13a, the production can be carried out byhydrolysis in water, organic solvent, or a mixture solvent in thepresence of an acid or a base.

Examples of the base that can be used include those described above forProcess 1 of Production method 1.

Use amount of the base can be appropriately selected from the range of0.01 to 100 mol per 1 mol of Formula 13a. Preferably, it is 0.1 to 10mol.

Examples of the acid that can be used include inorganic acids likehydrochloric acid, hydrobromic acid, and sulfuric acid, and organicacids like acetic acid and trifluoroacetic acid.

Use amount of the acid can be appropriately selected from the range of 1mol to excess amount per 1 mol of Formula 13a. Preferably, it is from 1to 100 mol.

Examples of the organic solvent that can be used include a mixturesolvent of water and an organic solvent. Examples of the organic solventinclude alcohols like methanol and ethanol, ether like tetrahydrofuran,ketones like acetone and methyl isobutyl ketone, amides likeN,N-dimethyl formamide and N,N-dimethyl acetamide, sulfur compounds likedimethyl sulfoxide and sulfolane, acetonitrile, and their mixture.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 13a.Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route f)

Specifically, compound of Formula 13b can be obtained by reacting thecompound of Formula 13a and a sulfurizing agent. In addition, thecompound of Formula 3b can be obtained by hydrolyzing the compound ofFormula 13b.

Use amount of the compound of the sulfurizing agent for the process ofproducing Formula 13b from Formula 13a can be appropriately selectedfrom the range of 1.0 to 8.0 mol per 1 mol of Formula 13a. Preferably,it is from 1.0 to 4.0 mol.

Examples of the sulfurizing agent that can be used include diphosphoruspentoxide and2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide.

Use amount of the compound of the sulfurizing agent can be appropriatelyselected from the range of 1.0 to 8.0 mol per 1 mol of Formula 13a.Preferably, it is 0.1 to 4.0 mol.

Examples of the solvent that can be used include those described abovefor Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

With regard to the process of obtaining the compound of Formula 3b fromthe compound of Formula 13b, the production can be carried out byhydrolysis in water, organic solvent, or a mixture solvent in thepresence of an acid or a base.

Examples of the base that can be used include those described above forProcess 1 of Production method 1.

Use amount of the base can be appropriately selected from the range of0.01 to 100 mol per 1 mol of Formula 13b. Preferably, it is 0.1 to 10mol.

Examples of the acid that can be used include inorganic acids likehydrochloric acid, hydrobromic acid, and sulfuric acid, and organicacids like acetic acid and trifluoroacetic acid.

Use amount of the acid can be appropriately selected from the range of 1mol to excess amount per 1 mol of Formula 13b. Preferably, it is from 1to 100 mol.

Examples of the organic solvent that can be used include a mixturesolvent of water and an organic solvent. Examples of the organic solventinclude alcohols like methanol and ethanol, ether like tetrahydrofuran,ketones like acetone and methyl isobutyl ketone, amides likeN,N-dimethyl formamide and N,N-dimethyl acetamide, sulfur compounds likedimethyl sulfoxide and sulfolane, acetonitrile, and their mixture.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 13b.Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 3b, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

<Intermediate Synthesis Method 1>

Compound of Formula 3a can be produced according to the method with thefollowing reaction scheme.

(in the formula, R¹, R², Y and Z each have the same definitions as aboveand X represents a chlorine or a bromine).

Specifically, Formula 3a can be produced by reacting Formula 3b and anappropriate halogenating agent with or without a solvent.

Examples of the halogenating agent that can be used include oxalylchloride and thionyl chloride.

Use amount of the halogenating agent can be appropriately selected fromthe range of 0.01 to 20 mol per 1 mol of Formula 3b. Preferably, it isfrom 1 to 10 mol.

Examples of the solvent include halogenated hydrocarbons likedichloromethane and chloroform, ethers like diethyl ether andtetrahydrofuran, and aromatic hydrocarbons like benzene and toluene.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 3b.Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. tothe boiling point of an inert solvent used. Preferably, the reaction iscarried out in the range of from 0° C. to 100° C. The reaction timevaries depending on the reaction temperature, the reaction substrates,the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 3a, i.e.,the target compound of this reaction, can be collected from the reactionsystem by general method, and if necessary, purified by a process likecolumn chromatography and recrystallization.

Examples of the production intermediates [13a] and [3b], that can bedescribed for the Production method 10, are shown in Table 44 to Table67.

TABLE 44

Compound No. R¹ R² Y Z IV-1  Me Me O O IV-2  Et Me O O IV-3  Pr-n Me O OIV-4  Pr-i Me O O IV-5  Bu-n Me O O IV-6  Bu-i Me O O IV-7  Bu-s Me O OIV-8  Bu-t Me O O IV-9  Hex-n Me O O IV-10 CH₂CF₃ Me O O IV-11 CH₂CH═CH₂Me O O IV-12 CH₂C(Me)═CH₂ Me O O IV-13 CH₂CH₂CH═CMe₂ Me O O IV-14CH₂C≡CH Me O O IV-15 CH₂C≡CCH₃ Me O O IV-16 Pr-c Me O O IV-17 Bu-c Me OO IV-18 Pen-c Me O O IV-19 Hex-c Me O O IV-20 CH₂Pr-c Me O O IV-21CH₂Bu-c Me O O IV-22 CH₂Pen-c Me O O IV-23 CH₂Hex-c Me O O IV-24CH₂CH═CCl2 Me O O IV-25 CH₂CCl═CHCl Me O O IV-26 CH₂CH₂CH═CCl₂ Me O OIV-27 CH₂CH₂C(Me)═CF₂ Me O O IV-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O IV-29CH₂CH═CF₂ Me O O IV-30 CH₂CH₂OMe Me O O IV-31 CH₂CH₂OEt Me O O IV-32CH(Me)CH₂OMe Me O O IV-33 CH₂CH₂OCH₂CH₂OMe Me O O IV-34 CH₂CH₂OPr-n Me OO IV-35 CH₂CH₂OPr-i Me O O IV-36 CH₂CH₂OPr-c Me O O

TABLE 45 Compound No. R¹ R² Y Z IV-37 CH₂CH₂OBu-c Me O O IV-38CH₂CH₂OPen-c Me O O IV-39 CH₂CH₂OHex-c Me O O IV-40 CH₂CH₂OCH₂CF₃ Me O OIV-41 CH₂CH₂CH₂OMe Me O O IV-42 CH═CHMe Me O O IV-43 CH₂SMe Me O O IV-44CH₂SPr-n Me O O IV-45 CH₂CH₂SMe Me O O IV-46 CH₂SOMe Me O O IV-47CH₂SO₂Me Me O O IV-48 CH₂CH₂CH₂SMe Me O O IV-49 CH₂CH₂CH₂SO₂Me Me O OIV-50 Ph Me O O IV-51 Ph(2-Cl) Me O O IV-52 Ph(3-Cl) Me O O IV-53Ph(4-Cl) Me O O IV-54 Ph(2-F) Me O O IV-55 Ph(3-F) Me O O IV-56 Ph(4-F)Me O O IV-57 Ph(2-Me) Me O O IV-58 Ph(3-Me) Me O O IV-59 Ph(4-Me) Me O OIV-60 Ph(2-OMe) Me O O IV-61 Ph(3-OMe) Me O O IV-62 Ph(4-OMe) Me O OIV-63 Ph(2-CF₃) Me O O IV-64 Ph(3-CF₃) Me O O IV-65 Ph(4-CF₃) Me O OIV-66 Ph(2-NO₂) Me O O IV-67 Ph(3-NO₂) Me O O IV-68 Ph(4-NO₂) Me O OIV-69 Ph(2-OCF₃) Me O O IV-70 Ph(3-OCF₃) Me O O IV-71 Ph(4-OCF₃) Me O OIV-72 Ph(2-CN) Me O O IV-73 Ph(3-CN) Me O O IV-74 Ph(4-CN) Me O O IV-75Ph(3,4-F₂) Me O O

TABLE 46 Compound No. R¹ R² Y Z IV-76 Ph(3,5-F₂) Me O O IV-77 Ph(2,3-F₂)Me O O IV-78 Ph(2,4-F₂) Me O O IV-79 Ph(2,5-F₂) Me O O IV-80 Ph(2,6-F₂)Me O O IV-81 Ph(3,4-Cl₂) Me O O IV-82 Ph(3,5-Cl₂) Me O O IV-83Ph(2,3-Cl₂) Me O O IV-84 Ph(2,4-Cl₂) Me O O IV-85 Ph(2,5-Cl₂) Me O OIV-86 Ph(2,6-Cl₂) Me O O IV-87 Ph(3,4-Me₂) Me O O IV-88 Ph(3,5-Me₂) Me OO IV-89 Ph(2,3-Me₂) Me O O IV-90 Ph(2,4-Me₂) Me O O IV-91 Ph(2,5-Me₂) MeO O IV-92 Ph(2,6-Me₂) Me O O IV-93 Ph(3,4-(OMe)₂) Me O O IV-94Ph(3,5-(OMe)₂) Me O O IV-95 Ph(2,3-(OMe)₂) Me O O IV-96 Ph(2,4-(OMe)₂)Me O O IV-97 Ph(2,5-(OMe)₂) Me O O IV-98 Ph(2,6-(OMe)₂) Me O O IV-99Ph(3-F-4-OMe) Me O O IV-100 Ph(3-F-5-OMe) Me O O IV-101 Ph(2-F-3-OMe) MeO O IV-102 Ph(2-F-4-OMe) Me O O IV-103 Ph(2-F-5-OMe) Me O O IV-104Ph(2-F-6-OMe) Me O O IV-105 Ph(3-F-4-Me) Me O O IV-106 Ph(3-F-5-Me) Me OO IV-107 Ph(2-F-3-Me) Me O O IV-108 Ph(2-F-4-Me) Me O O IV-109Ph(2-F-5-Me) Me O O IV-110 Ph(2-F-6-Me) Me O O IV-111 Ph(3-OMe-4-F) Me OO IV-112 Ph(2-OMe-3-F) Me O O IV-113 Ph(2-OMe-4-F) Me O O IV-114Ph(2-OMe-5-F) Me O O

TABLE 47 Compound No. R¹ R² Y Z IV-115 Ph(3-Me-4-F) Me O O IV-116Ph(2-Me-3-F) Me O O IV-117 Ph(2-Me-4-F) Me O O IV-118 Ph(2-Me-5-F) Me OO IV-119 Ph(3-Cl-4-OMe) Me O O IV-120 Ph(3-Cl-5-OMe) Me O O IV-121Ph(2-Cl-3-OMe) Me O O IV-122 Ph(2-Cl-4-OMe) Me O O IV-123 Ph(2-Cl-5-OMe)Me O O IV-124 Ph(2-Cl-6-OMe) Me O O IV-125 Ph(3-Cl-4-Me) Me O O IV-126Ph(3-Cl-5-Me) Me O O IV-127 Ph(2-Cl-3-Me) Me O O IV-128 Ph(2-Cl-4-Me) MeO O IV-129 Ph(2-Cl-5-Me) Me O O IV-130 Ph(2-Cl-6-Me) Me O O IV-131Ph(3-OMe-4-Cl) Me O O IV-132 Ph(2-OMe-3-Cl) Me O O IV-133 Ph(2-OMe-4-Cl)Me O O IV-134 Ph(2-OMe-5-Cl) Me O O IV-135 Ph(3-Me-4-Cl) Me O O IV-136Ph(2-Me-3-Cl) Me O O IV-137 Ph(2-Me-4-Cl) Me O O IV-138 Ph(2-Me-5-Cl) MeO O IV-139 Ph(3-F-4-C1) Me O O IV-140 Ph(3-F-5-Cl) Me O O IV-141Ph(2-F-3-Cl) Me O O IV-142 Ph(2-F-4-Cl) Me O O IV-143 Ph(2-F-5-Cl) Me OO IV-144 Ph(2-F-6-Cl) Me O O IV-145 Ph(3-Cl-4-F) Me O O IV-146Ph(2-Cl-3-F) Me O O IV-147 Ph(2-Cl-4-F) Me O O IV-148 Ph(2-Cl-5-F) Me OO IV-149 Ph(3-Me-4-OMe) Me O O IV-150 Ph(3-Me-5-OMe) Me O O IV-151Ph(2-Me-3-OMe) Me O O IV-152 Ph(2-Me-4-OMe) Me O O IV-153 Ph(2-Me-5-OMe)Me O O

TABLE 48 Compound No. R¹ R² Y Z IV-154 Ph(2-Me-6-OMe) Me O O IV-155Ph(3-OMe-4-Me) Me O O IV-156 Ph(2-OMe-3-Me) Me O O IV-157 Ph(2-OMe-4-Me)Me O O IV-158 Ph(2-OMe-5-Me) Me O O IV-159 Ph(3-CN-4-OMe) Me O O IV-160Ph(3-OMe-4-CN) Me O O IV-161 Ph(3-Me-4-CN) Me O O IV-162 Ph(3-CN-4-Me)Me O O IV-163 Ph(3-NO₂-4-OMe) Me O O IV-164 Ph(3-OMe-4-NO₂) Me O OIV-165 Ph(3-Me-4-NO₂) Me O O IV-166 Ph(3-NO₂-4-Me) Me O O IV-167Ph(3,5-F₂-5-OMe) Me O O IV-168 Ph(3,5-F₂-5-Me) Me O O IV-169Ph(3,4,5-(OMe)₃) Me O O IV-170

Me O O IV-171

Me O O IV-172

Me O O IV-173

Me O O IV-174

Me O O IV-175

Me O O IV-176

Me O O IV-177

Me O O

TABLE 49 Compound No. R¹ R² Y Z IV-178

Me O O IV-179

Me O O IV-180

Me O O IV-181

Me O O IV-182

Me O O IV-183

Me O O IV-184

Me O O IV-185

Me O O IV-186

Me O O IV-187

Me O O IV-188

Me O O IV-189

Me O O IV-190

Me O O IV-191

Me O O

TABLE 50 Compound No. R¹ R² Y Z IV-192

Me O O IV-193

Me O O IV-194

Me O O IV-195

Me O O IV-196

Me O O IV-197

Me O O IV-198

Me O O IV-199

Me O O IV-200

Me O O IV-201

Me O O IV-202

Me O O IV-203

Me O O IV-204

Me O

TABLE 51 Compound No. R¹ R² Y Z IV-205 CH₂Ph Me O O IV-206 CH₂CH₂Ph Me OO IV-207 CH₂CH₂CH₂Ph Me O O IV-208 CH₂CH═CHPh Me O O IV-209 CH₂C≡CPh MeO O IV-210 CH₂CH═NOMe Me O O IV-211 CH₂CH═NOEt Me O O IV-212CH₂CH═NOPr-n Me O O IV-213 CH₂CH═NOPh Me O O IV-214 CH₂CH(OMe)₂ Me O OIV-215 CH₂CHO Me O O IV-216 NH₂ Me O O IV-217 NHMe Me O O IV-218 NHEt MeO O IV-219 NHPr-n Me O O IV-220 NHPr-i Me O O IV-221 NHBu-n Me O OIV-222 NHBu-i Me O O IV-223 NHBu-s Me O O IV-224 NHCH₂Pr-c Me O O IV-225NHPen-n Me O O IV-226 NHHex-n Me O O IV-227 NHCH₂CH₂CH₂Cl Me O O IV-228NHCH₂CH₂CH₂F Me O O IV-229 NHCH₂CH₂OMe Me O O IV-230 NMe₂ Me O O IV-231NEt₂ Me O O IV-232 N(Pr-n)₂ Me O O IV-233 N(Bu-n)₂ Me O O IV-234 N(Me)EtMe O O IV-235 N(Me)CH₂CH₂OMe Me O O IV-236 NHPh Me O O IV-237 NHCH₂Ph MeO O IV-238 N═CMe₂ Me O O IV-239 N═CEt₂ Me O O IV-240 N═CHNMe₂ Me O OIV-241 NHC(═O)Me Me O O IV-242 N[C(═O)Me]₂ Me O O IV-243 NHC(═O)OMe Me OO IV-244 N[C(═O)OMe]₂ Me O O IV-245 NHSO₂Me Me O O

TABLE 52 Compound No. R¹ R² Y Z IV-246 NHSO₂Ph Me O O IV-247 NHSO₂CH₂PhMe O O IV-248 OMe Me O O IV-249 OEt Me O O IV-250 OPr-n Me O O IV-251OPr-i Me O O IV-252 OCH₂Pr-c Me O O IV-253 OCH₂Cl Me O O IV-254 OCHCl₂Me O O IV-255 OCCl₃ Me O O IV-256 OCH₂F Me O O IV-257 OCHF₂ Me O OIV-258 OCF₃ Me O O IV-259 Ph Et O O IV-260 Ph Pr-i O O IV-261 Ph CHF₂ OO IV-262 Ph Ph O O IV-263 Ph Me O S IV-264 Ph Me S S IV-265 Me Me O SIV-266 Me Me S S IV-267 Ph Me O O IV-268 Ph(4-OEt) Me O O IV-269Ph(2-Ph) Me O O IV-270 Ph(3-Ph) Me O O IV-271 Ph(4-Ph) Me O O IV-272

Me O O IV-273

Me O O IV-274 Me

O O IV-275 Et

O O IV-276

Me O O

TABLE 53 Compound No. R¹ R² Y Z IV-277

Me O O IV-278

Me O O IV-279

Me O O IV-280

Me O O IV-281

Me O O IV-282 Ph(2-Me-4-Br) O O IV-283 Ph(2-Me-4-I) Me O O IV-284Ph(2-Me-4-CF₃) Me O O IV-285 Ph(2-Me-4-OCF₃) Me O O IV-286 Ph(2-Pr-i) MeO O IV-287

Me O O IV-288 Ph(2-Et) Me O O IV-289

Me O O IV-290

Me O O IV-291

Me O S IV-292

Me O O IV-293

Me O O IV-294 CH₂COOBu-t Me O O IV-295 (C₇H₁₄)CH₃ Me O O IV-296(C₉H₁₈)CH₃ Me O O IV-297 Ph(2-F,4-Cl,5-OMe) Me O O IV-298Ph(2,3,4-(OMe)₃) Me O O IV-299 Ph(3,5-Cl₂-4-OMe) Me O O IV-300Ph(3,5-Cl₂-4-SMe) Me O O

TABLE 54 Compound No. R¹ R² Y Z IV-301 Ph(3,5-Cl₂-4-SO₂Me) Me O O IV-302Ph(3,4,5-F₃) Me O O IV-303

Me O O IV-304

Me O O IV-305

Me O O IV-306 Bu-n

O O IV-307 CH₂CH(CH₃)₂

O O IV-308 Ph Pen-n O O IV-309 H Me O O IV-310 CH₂C≡CF Me O O IV-311

Me O O IV-312

Me O O IV-313 CH₂NH₂ Me O O IV-314 CH₂NO₂ Me O O IV-315 CH₂NHCH₃ Me O OIV-316 CH₂N(CH₃)₂ Me O O IV-317 CH₂SCH₂CF₃ Me O O IV-318 CH₂SOCH₂CF₃ MeO O IV-319 CH₂SO₂CH₂CF₃ Me O O IV-320 CH₂OH Me O O IV-321 CH₂OBn Me O OIV-322 CH₂OCH₂Pr-c Me O O IV-323 CH₂OPh Me O O IV-324 CH₂SPh Me O OIV-325 CH₂SOPh Me O O IV-326 CH₂SO₂Ph Me O O IV-327 CH₂CON(CH₃)₂ Me O OIV-328 CH₂COCH₃ Me O O IV-329 CH₂OCOCH₃ Me O O

TABLE 55 Com- pound No. R¹ R² Y Z IV-330 CH₂ON═CHCH₃ Me O O IV-331C₂H₄OC₂H₄SCH₃ Me O O IV-332 C₂H₄OC₂H₄SOCH₃ Me O O IV-333 C₂H₄OC₂H₄SO₂CH₃Me O O IV-334 CH₂OCH₂CN Me O O IV-335 CH₂CN Me O O IV-336 OCH₂CH═CH₂ MeO O IV-337 OCH₂C≡CH Me O O IV-338 OPr-c Me O O IV-339

Me O O IV-340

Me O O IV-341

Me O O IV-342

Me O O IV-343

Me O O IV-344 Ph H O O IV-345 Ph CH₂CH═CH₂ O O IV-346 Ph CH₂C≡CH O OIV-347 Ph Pr-c O O IV-348 Ph CH₂CH═CF₂ O O IV-349 Ph CH₂C≡CF O O IV-350Ph C₂H₄OCH₃ O O IV-351 Ph C₂H₄OC₂H₅ O O IV-352 Ph CH(Me)OEt O O IV-353Ph CH₂OPr-c O O IV-354 Ph CH(OCH₃)₂ O O IV-355 Ph CH₂Ph O O IV-356 PhCH═CH—Ph O O IV-357 Ph C≡C—Ph O O

TABLE 56

Compound No. R¹ R² Y Z V-1  Me Me O O V-2  Et Me O O V-3  Pr-n Me O OV-4  Pr-i Me O O V-5  Bu-n Me O O V-6  Bu-i Me O O V-7  Bu-s Me O O V-8 Bu-t Me O O V-9  Hex-n Me O O V-10 CH₂CF₃ Me O O V-11 CH₂CH═CH₂ Me O OV-12 CH₂C(Me)═CH₂ Me O O V-13 CH₂CH₂CH═CMe₂ Me O O V-14 CH₂C≡CH Me O OV-15 CH₂C≡CCH₃ Me O O V-16 Pr-c Me O O V-17 Bu-c Me O O V-18 Pen-c Me OO V-19 Hex-c Me O O V-20 CH₂Pr-c Me O O V-21 CH₂Bu-c Me O O V-22CH₂Pen-c Me O O V-23 CH₂Hex-c Me O O V-24 CH₂CH═CCl₂ Me O O V-25CH₂CCl═CHCl Me O O V-26 CH₂CH₂CH═CCl₂ Me O O V-27 CH₂CH₂C(Me)═CF₂ Me O OV-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O V-29 CH₂CH═CF₂ Me O O V-30 CH₂CH₂OMeMe O O V-31 CH₂CH₂OEt Me O O V-32 CH(Me)CH₂OMe Me O O V-33CH₂CH₂OCH₂CH₂OMe Me O O V-34 CH₂CH₂OPr-n Me O O V-35 CH₂CH₂OPr-i Me O OV-36 CH₂CH₂OPr-c Me O O V-37 CH₂CH₂OBu-c Me O O V-38 CH₂CH₂OPen-c Me O O

TABLE 57 Compound No. R¹ R² Y Z V-39 CH₂CH₂OHex-c Me O O V-40CH₂CH₂OCH₂CF₃ Me O O V-41 CH₂CH₂CH₂OMe Me O O V-42 CH═CHMe Me O O V-43CH₂SMe Me O O V-44 CH₂SPr-n Me O O V-45 CH₂CH₂SMe Me O O V-46 CH₂SOMe MeO O V-47 CH₂SO₂Me Me O O V-48 CH₂CH₂CH₂SMe Me O O V-49 CH₂CH₂CH₂SO₂Me MeO O V-50 Ph Me O O V-51 Ph(2-Cl) Me O O V-52 Ph(3-Cl) Me O O V-53Ph(4-Cl) Me O O V-54 Ph(2-F) Me O O V-55 Ph(3-F) Me O O V-56 Ph(4-F) MeO O V-57 Ph(2-Me) Me O O V-58 Ph(3-Me) Me O O V-59 Ph(4-Me) Me O O V-60Ph(2-OMe) Me O O V-61 Ph(3-OMe) Me O O V-62 Ph(4-OMe) Me O O V-63Ph(2-CF₃) Me O O V-64 Ph(3-CF₃) Me O O V-65 Ph(4-CF₃) Me O O V-66Ph(2-NO₂) Me O O V-67 Ph(3-NO₂) Me O O V-68 Ph(4-NO₂) Me O O V-69Ph(2-OCF₃) Me O O V-70 Ph(3-OCF₃) Me O O V-71 Ph(4-OCF₃) Me O O V-72Ph(2-CN) Me O O V-73 Ph(3-CN) Me O O V-74 Ph(4-CN) Me O O V-75Ph(3,4-F₂) Me O O V-76 Ph(3,5-F₂) Me O O V-77 Ph(2,3-F₂) Me O O V-78Ph(2,4-F₂) Me O O

TABLE 58 Compound No. R¹ R² Y Z V-79 Ph(2,5-F₂) Me O O V-80 Ph(2,6-F₂)Me O O V-81 Ph(3,4-Cl₂) Me O O V-82 Ph(3,5-Cl₂) Me O O V-83 Ph(2,3-Cl₂)Me O O V-84 Ph(2,4-Cl₂) Me O O V-85 Ph(2,5-Cl₂) Me O O V-86 Ph(2,6-Cl₂)Me O O V-87 Ph(3,4-Me₂) Me O O V-88 Ph(3,5-Me₂) Me O O V-89 Ph(2,3-Me₂)Me O O V-90 Ph(2,4-Me₂) Me O O V-91 Ph(2,5-Me₂) Me O O V-92 Ph(2,6-Me₂)Me O O V-93 Ph(3,4-(OMe)₂) Me O O V-94 Ph(3,5-(OMe)₂) Me O O V-95Ph(2,3-(OMe)₂) Me O O V-96 Ph(2,4-(OMe)₂) Me O O V-97 Ph(2,5-(OMe)₂) MeO O V-98 Ph(2,6-(OMe)₂) Me O O V-99 Ph(3-F-4-OMe) Me O O V-100Ph(3-F-5-OMe) Me O O V-101 Ph(2-F-3-OMe) Me O O V-102 Ph(2-F-4-OMe) Me OO V-103 Ph(2-F-5-OMe) Me O O V-104 Ph(2-F-6-OMe) Me O O V-105Ph(3-F-4-Me) Me O O V-106 Ph(3-F-5-Me) Me O O V-107 Ph(2-F-3-Me) Me O OV-108 Ph(2-F-4-Me) Me O O V-109 Ph(2-F-5-Me) Me O O V-110 Ph(2-F-6-Me)Me O O V-111 Ph(3-OMe-4-F) Me O O V-112 Ph(2-OMe-3-F) Me O O V-113Ph(2-OMe-4-F) Me O O V-114 Ph(2-OMe-5-F) Me O O V-115 Ph(3-Me-4-F) Me OO V-116 Ph(2-Me-3-F) Me O O V-117 Ph(2-Me-4-F) Me O O

TABLE 59 Compound No. R¹ R² Y Z V-118 Ph(2-Me-5-F) Me O O V-119Ph(3-Cl-4-OMe) Me O O V-120 Ph(3-Cl-5-OMe) Me O O V-121 Ph(2-Cl-3-OMe)Me O O V-122 Ph(2-Cl-4-OMe) Me O O V-123 Ph(2-Cl-5-OMe) Me O O V-124Ph(2-Cl-6-OMe) Me O O V-125 Ph(3-Cl-4-Me) Me O O V-126 Ph(3-Cl-5-Me) MeO O V-127 Ph(2-Cl-3-Me) Me O O V-128 Ph(2-Cl-4-Me) Me O O V-129Ph(2-Cl-5-Me) Me O O V-130 Ph(2-Cl-6-Me) Me O O V-131 Ph(3-OMe-4-Cl) MeO O V-132 Ph(2-OMe-3-Cl) Me O O V-133 Ph(2-OMe-4-Cl) Me O O V-134Ph(2-OMe-5-Cl) Me O O V-135 Ph(3-Me-4-Cl) Me O O V-136 Ph(2-Me-3-Cl) MeO O V-137 Ph(2-Me-4-Cl) Me O O V-138 Ph(2-Me-5-Cl) Me O O V-139Ph(3-F-4-Cl) Me O O V-140 Ph(3-F-5-Cl) Me O O V-141 Ph(2-F-3-Cl) Me O OV-142 Ph(2-F-4-Cl) Me O O V-143 Ph(2-F-5-Cl) Me O O V-144 Ph(2-F-6-Cl)Me O O V-145 Ph(3-Cl-4-F) Me O O V-146 Ph(2-Cl-3-F) Me O O V-147Ph(2-Cl-4-F) Me O O V-148 Ph(2-Cl-5-F) Me O O V-149 Ph(3-Me-4-OMe) Me OO V-150 Ph(3-Me-5-OMe) Me O O V-151 Ph(2-Me-3-OMe) Me O O V-152Ph(2-Me-4-OMe) Me O O V-153 Ph(2-Me-5-OMe) Me O O V-154 Ph(2-Me-6-OMe)Me O O V-155 Ph(3-OMe-4-Me) Me O O V-156 Ph(2-OMe-3-Me) Me O O

TABLE 60 Compound No. R¹ R² Y Z V-157 Ph(2-OMe-4-Me) Me O O V-158Ph(2-OMe-5-Me) Me O O V-159 Ph(3-CN-4-OMe) Me O O V-160 Ph(3-OMe-4-CN)Me O O V-161 Ph(3-Me-4-CN) Me O O V-162 Ph(3-CN-4-Me) Me O O V-163Ph(3-NO₂-4-OMe) Me O O V-164 Ph(3-OMe-4-NO₂) Me O O V-165 Ph(3-Me-4-NO₂)Me O O V-166 Ph(3-NO₂-4-Me) Me O O V-167 Ph(3,5-F₂-4-OMe) Me O O V-168Ph(3,5-F₂-4-Me) Me O O V-169 Ph(3,4,5-(OMe)₃) Me O O V-170

Me O O V-171

Me O O V-172

Me O O V-173

Me O O V-174

Me O O V-175

Me O O V-176

Me O O V-177

Me O O V-178

Me O O

TABLE 61 Compound No. R¹ R² Y Z V-179

Me O O V-180

Me O O V-181

Me O O V-182

Me O O V-183

Me O O V-184

Me O O V-185

Me O O V-186

Me O O V-187

Me O O V-188

Me O O V-189

Me O O V-190

Me O O V-191

Me O O V-192

Me O O

TABLE 62 Compound No. R¹ R² Y Z V-193

Me O O V-194

Me O O V-195

Me O O V-196

Me O O V-197

Me O O V-198

Me O O V-199

Me O O V-200

Me O O V-201

Me O O V-202

Me O O V-203

Me O O V-204

Me O O V-205 CH₂Ph Me O O V-206 CH₂CH₂Ph Me O O V-207 CH₂CH₂CH₂Ph Me O OV-208 CH₂CH═CHPh Me O O V-209 CH₂C≡CPh Me O O V-210 CH₂CH═NOMe Me O O

TABLE 63 Compound No. R¹ R² Y Z V-211 CH₂CH═NOEt Me O O V-212CH₂CH═NOPr-n Me O O V-213 CH₂CH═NOPh Me O O V-214 CH₂CH(OMe)₂ Me O OV-215 CH₂CHO Me O O V-216 NH₂ Me O O V-217 NHMe Me O O V-218 NHEt Me O OV-219 NHPr-n Me O O V-220 NHPr-i Me O O V-221 NHBu-n Me O O V-222 NHBu-iMe O O V-223 NHBu-s Me O O V-224 NHCH₂Pr-c Me O O V-225 NHPen-n Me O OV-226 NHHex-n Me O O V-227 NHCH₂CH₂CH₂Cl Me O O V-228 NHCH₂CH₂CH₂F Me OO V-229 NHCH₂CH₂OMe Me O O V-230 NMe₂ Me O O V-231 NEt₂ Me O O V-232N(Pr-n)₂ Me O O V-233 N(Bu-n)₂ Me O O V-234 N(Me)Et Me O O V-235N(Me)CH₂CH₂OMe Me O O V-236 NHPh Me O O V-237 NHCH₂Ph Me O O V-238N═CMe₂ Me O O V-239 N═CEt₂ Me O O V-240 N═CHNMe₂ Me O O V-241 NHC(═O)MeMe O O V-242 N[C(═O)Me]₂ Me O O V-243 NHC(═O)OMe Me O O V-244N[C(═O)OMe]₂ Me O O V-245 NHSO₂Me Me O O V-246 NHSO₂Ph Me O O V-247NHSO₂CH₂Ph Me O O V-248 OMe Me O O V-249 OEt Me O O V-250 OPr-n Me O OV-251 OPr-i Me O O V-252 OCH₂Pr-c Me O O V-253 OCH₂Cl Me O O V-254OCHCl₂ Me O O

TABLE 64 Compound No. R¹ R² Y Z V-255 OCCl₃ Me O O V-256 OCH₂F Me O OV-257 OCHF₂ Me O O V-258 OCF₃ Me O O V-259 Ph Et O O V-260 Ph Pr-i O OV-261 Ph CHF₂ O O V-262 Ph Ph O O V-263 Ph Me O S V-264 Ph Me S S V-265Me Me O S V-266 Me Me S S V-267 Ph Me O O V-268 Ph(4-OEt) Me O O V-269Ph(2-Ph) Me O O V-270 Ph(3-Ph) Me O O V-271 Ph(4-Ph) Me O O V-272

Me O O V-273

Me O O V-274 Me

O O V-275 Et

O O V-276

Me O O V-277

Me O O V-278

Me O O V-279

Me O O

TABLE 65 Compound No. R¹ R² Y Z V-280

Me O O V-281

Me O O V-282 Ph(2-Me-4-Br) Me O O V-283 Ph(2-Me-5-I) Me O O V-284Ph(2-Me-5-CF₃) Me O O V-285 Ph(2-Me-6-OCF₃) Me O O V-286 Ph(2-Pr-i) Me OO V-287

Me O O V-288 Ph(2-Et) Me O O V-289

Me O O V-290

Me O O V-291

Me O S V-292

Me O O V-293

Me O O V-294 CH₂COOBu-t Me O O V-295 (C₇H₁₄)CH₃ Me O O V-296 (C₉H₁₈)CH₃Me O O V-297 Ph(2-F,4-Cl,5-OMe) Me O O V-298 Ph(2,3,4-(OMe)₃) Me O OV-299 Ph(3,5-Cl₂-4-OMe) Me O O V-300 Ph(3,5-Cl₂-4-SMe) Me O O V-301Ph(3,5-Cl₂-4-SO₂Me) Me O O V-302 Ph(3,4,5-F₃) Me O O V-303

Me O O

TABLE 66 Compound No. R¹ R² Y Z V-304

Me O O V-305

Me O O V-306 Bu-n

O O V-307 CH₂CH(CH₃)₂

O O V-308 Ph Pen-n O O V-309 H Me O O V-310 CH₂C≡CF Me O O V-311

Me O O V-312

Me O O V-313 CH₂NH₂ Me O O V-314 CH₂NO₂ Me O O V-315 CH₂NHCH₃ Me O OV-316 CH₂N(CH₃)₂ Me O O V-317 CH₂SCH₂CF₃ Me O O V-318 CH₂SOCH₂CF₃ Me O OV-319 CH₂SO₂CH₂CF₃ Me O O V-320 CH₂OH Me O O V-321 CH₂OBn Me O O V-322CH₂OCH₂Pr-c Me O O V-323 CH₂OPh Me O O V-324 CH₂SPh Me O O V-325 CH₂SOPhMe O O V-326 CH₂SO₂Ph Me O O V-327 CH₂CON(CH₃)₂ Me O O V-328 CH₂COCH₃ MeO O V-329 CH₂OCOCH₃ Me O O V-330 CH₂ON═CHCH₃ Me O O V-331 C₂H₄OC₂H₄SCH₃Me O O V-332 C₂H₄OC₂H₄SOCH₃ Me O O V-333 C₂H₄OC₂H₄SO₂CH₃ Me O O

TABLE 67 Compound No. R¹ R² Y Z V-334 CH₂OCH₂CN Me O O V-335 CH₂CN Me OO V-336 OCH₂CH═CH₂ Me O O V-337 OCH₂C≡CH Me O O V-338 OPr-c Me O O V-339

Me O O V-340

Me O O V-341

Me O O V-342

Me O O V-343

Me O O V-344 Ph H O O V-345 Ph CH₂CH═CH₂ O O V-346 Ph CH₂C≡CH O O V-347Ph Pr-c O O V-348 Ph CH₂CH═CF₂ O O V-349 Ph CH₂C≡CF O O V-350 PhC₂H₄OCH₃ O O V-351 Ph C₂H₄OC₂H₅ O O V-352 Ph CH(Me)OEt O O V-353 PhCH₂OPr-c O O V-354 Ph CH(OCH₃)₂ O O V-355 Ph CH₂Ph O O V-356 Ph CH═CH—PhO O V-357 Ph C≡C—Ph O O V-358 Ph(3,4,5-Cl) Me O O V-359 N(Me)Ph Me O OV-360

Me O O V-361

Me O O V-362 CH₂CO(Bu-t) Me O O V-363 Ph(2,3,5,6-F₄) Me O O V-364Ph[(3,5-(CF₃)₂] Me O O V-365 CH₂C(Me)═NOMe Me O O V-366 Ph(2,4,6-Me₃) MeO O V-367 Ph(2,3,4,5,6-F₅) Me O O V-368 N(Et)Ph Me O O V-369 N(Pr-i)PhMe O O V-370 N(Me)Ph(4-F) Me O O V-371 CH₂C(Me)═NOEt Me O O

Compounds of the invention have an excellent herbicidal activity andsome of them show excellent selectivity between crops and weeds and areuseful as an agrochemical composition for farmland, especially asherbicides. In other words, the compounds of the invention have aherbicidal activity for various woods during foliage treatment, soiltreatment, seed dressing treatment, soil blending treatment, soiltreatment before sowing, treatment at the time of sowing, soil treatmentafter sowing, soil covering and blending treatment at the time ofsowing, and soil treatment before and after sowing for no-tillagefarming of a field for cultivating agrohorticultural plants.

Hereinbelow, examples of the weeds are given, but the invention is notlimited to them;

weeds of Onagraceae family Oenothera erythrosepala, Oenothera laciniata;

weeds of Ranunculaceae family: Ranunculus muricatus, Ranunculus sardous;

weeds of Polygonaceae family: Polygonum convolvulus, Polygonumlapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Rumexcrispus, Rumex obtusifolius, Poligonum cuspidatum, Polygonumpensylvanicum, Persicaria longiseta, Persicaria lapathifolia, Persicarianepalensis;

weeds of Portulacaceae family: Portulaca oleracea;

weeds of Caryophyllaceae family: Stellaria media, Cerastium glomeratum,Stellaria alsine, Spergula arvensis, Stellaria aquatica;

weeds of Chenopodiaccae family: Chenopodium album, Kochia scoparia,Chenopodium album, Chenopodium ficifolium;

weeds of Amaranthaceae family: Amaranthus retroflexus, Amaranthushybridus, Amaranthus palmeri, Amaranthus spinosus, Amaranthus rudis,Amaranthus albus, Amaranthus viridus, Amaranthus lividus;

weeds of Brassicaceae family: Raphanus raphanistrum, Sinapis arvensis,Capsella bursa-pastoris, Lepidium virginicum, Thlaspi arvense,Descurarinia sophia, Rorippa indica, Rorippa islandica, Sisymnriumofficinale, Cardamine flexuosa, Nasturtium officinale, Draba nemorosa;

weeds of Fabaceae family: Sesbania exaltata, Cassia obtusifolia,Desmodium tortuosum, Trifolium repens, Vicia sativa, Medicago lupulina,Vicia hirsuta; Kummerowia striata, Medicago polymorpha, Viciaangustifolia, Aeschynomene indica;

weeds of Malvaceae family: Abutilon theophrasti, Sida spinosa;

weeds of Violet family: Viola arvensis, Viola tricolor,

weeds of Rubiaceae family: Galium aparine;

weeds of Convolvulaceae family: Ipomoea hederacea, Ipomoea purpurea,Ipomoea hederacea var integriuscula, Ipomoea lacunosa, Convolvulusarvensis, Ipomoea indica, Ipomoea coccinea, Ipomoea triloba;

weeds of Lamiaceae family: Lamium purpureum, Lamium amplexicaule,Stachys arvensis;

weeds of Solanaceae family: Datura stramonium, Solanum nigrum, Physalisangulata, Solanum americanum, Solanum carolinense;

weeds of Scrophulariaceae family: Veronica persica, Veronica arvensis,Veronica hederaefolia;

weeds of Asteraceae family: Xanthium pensylvanicum, Helianthus annuus,Matricaria chamomilla, Matricaria perforata or inodora, Chrysanthemumsegetum, Matricaria matricarioides, Ambrosia artemisiifolia, Ambrosiatrifida, Erigeron canadensis, Artemisia princeps, Solidago altissima,Taraxacum officinale, Anthemis cotula, Breca setosa, Sonchus oleraceus,Helianthus tuberosus, Cirsium arvense, Bidens frondosa, Bidens pilosa,Centurea cyanus, Cirsium vulgare, Lactuca scariola, Rudbeckia hirta,Rudbeckia laciniata, Rudbeckia laciniata var. hortensis Bailey, Seneciovulgais, Silybum marianum, Sonchus asper, Sonchus arvensis, Salsolakali, Bidens ftondosa, Eclipta ptostrata, Bidense tipartita, Seneciomadagascariensis, Coreopsis lanceolata, Rudbeckia laciniata;

weeds of Boraginaceae family: Myosotis arvensis;

weeds of Asclepiadaceae family: Asclepias syriaca;

weeds of Euphorbiaceae family: Euphorbia helioscopia, Euphorbiamaculata, Acalypha australis;

weeds of Geraniaceae family: Geranium carolinianum;

weeds of Oxalidaceae family: Oxalis corymbosa;

weeds of Cucurbitaceae family: Sicyos angulatus;

weeds of Poaceae family: Echinochloa crus-galli, Setaria viridis,Setaria faberi, Digitaria sanguinalis, Eleusine indica, Poa annua,Alopecurus myosuroides, Avena fatua, Sorghum halepense, Agropyronrepens, Bromus tectorum, Cynodone dactylon, Panicum dichotomiflorum,Panicum texanum, Sorghum vulgare, Alopecurus geniculatus, Loliummultiflorum, Lolium rigidum, Setaria glauca, Beckmannia syzigachne;

weeds of Commelinaceae family: Commelina communis;

weeds of Equisetaceae family: Equisetum arvense;

weeds of Papaveracea family Papaver rhoeas;

weeds of Cyperaceae family: Cyperus iria, Cyperus rotundus, Cyperusesculentus.

Compounds of the invention do not exhibit any phytotoxicity which causesa problem in major crops like Zea mays, Triticum aestivum, Hordeumvulgare, Oryza sativa, Sorghum bicolor, Glycine max, Gossypium spp.,Beta vulgaris, Arachis hypogaea, Helianthus annuus, Brassica napus, buckwheat, sugar cane, and tobacco, and horticultural crops like flowers andvegetables.

Further, the compounds of the invention are useful for effectiveelimination of various weeds which cause a trouble in no-tillage farmingof soybean, corn, and wheat, and they do not exhibit any problematicphytotoxicity to crops.

According to many treatment methods like soil treatment beforecultivation; soil treatment after cultivation but before or aftersowing; soil treatment after harrowing but before or after sowing, ortreatment before or after transplanting a seedling; treatment at thetime of transplanting a seedling; desalination treatment aftertransplanting a seedling; and foliage treatment, the compounds of theinvention can exhibit an herbicidal activity for many problematic weedsin paddy field that are described below.

Hereinbelow, examples of the weeds are given, but the invention is notlimited to them:

weeds of Poaceae family: Echinochloa oryzicola; Echinochloa crus-galli,Leptochloa chinensis, Isachne globosa, Paspalum distichum, Leersiasayanuka, Leersia oryzoides;

weeds of Scrophulariaceae family: Lindemia procumbens, Lindenia dubia,Dopatrium junceum, Gratiolajaponica, Lindernia angustifolia, Limnophilasessiliflora;

weeds of Lythraceae family: Rotala indica, Ammannia multiflora;

weeds of Elatinacease family: Elatine triandra;

weeds of Cypcracease family: Cyperus difformis, Scirpus hotarui,Eleocharis acicularis, Cyperus scrotinus, Eleocharis kuroguwai,Fimbristylis miliacea, Cyperus flaccidus, Cyperus globosus, Scirpusjuncoides, Scirpus wallichii, Scirpus nipponicus, Fimbristylisautumnalis, Scirpus tabernaemontani, Scirpus juncoides Rocxb., Scirpuslineolatus Franch. et Savat., Cyperus orthostachyus Franch. et Savat.,Cyperus orthostachyus Franch. et Savat., Eleocharis congesta D. Don,Scirpus planiculmis Fr. Schm.;

weeds of Pontederiacease family: Monochoria vaginalis, Monochoriakorsakowii, Heteranthera limosa;

weeds of Alismatacease family: Sagittaria pygmaea, Sagittaria trifolia,Alisma canaliculatum, Sagittaria aginashi;

weeds of Potamogetonacease family: Potamogeton distinctus;

weeds of Eruocaulacease family: Eriocaulon cinercum;

weeds of Apiacease family: Oenanthe javanica;

weeds of Asteracease family: Eclipta prostrata, Bidens tripartita;

weeds of Commelinacease family: Murdannia keisak;

weeds of Characease family: Chara braunii;

weeds of Lemnacease family: Spirodela polyrhiza;

Hepaticae: Ricciocarpus natans;

Zygnemataceae: Spirogyra arcla.

Further, the compounds of the invention show no phytoxicity to paddyrice according to any cultivation method including direct sowing ortransplanting of paddy rice followed by cultivation.

Further, the compounds of the invention can be used for controlling awide spectrum of weeds thriving in a lot for industrial facilities likea slope of a levee, a riverbed, a shoulder and a slope of a mad, arailway site, park spaces, grand, a parking lot, an airport, a factoryand a storage facility, a non-crop land like fallow fields, and vacantlots in city, which needs the weed control, or an orchard, a pastureland, a grass land, a forest land, etc.

Moreover, according to foliage treatment, water-surface application,etc., the compounds of the invention can exhibit a herbicidal activityfor water weeds which occur in river, waterway, canal, reservoir, etc.,wherein the water weeds include Pontederiaceae family: Eichhorniacrassipes; Salvinia natans family: Azolla imbricata, Azolla japonica,Salvinia natanas; Araceae family: Pistia stratiotes; Haloragaceaefamily: Myriophyllum brasilonsa, Myriophyllum verticillatum;Myriophyllum spicatum; Myriophyllum matogrossense; Azollaceae family:Azolla cristata; Scrophulariaccase family: Veronica anagallis-aquatica;Amaranthaceae family: Alternanthera philoxeroides; Gymnocoronisspilanthoides; Poaceate family: Spartina anglica; Apiaceae family:Hydrocotyle ranunculoides; Hydrocharitaceae family: Hydrillaverticillata, Egeria densa; Cabpmbaceae family: Cabomba caroliniana; andLemnaceae family: Wolffia globosa.

The agrohorticultural plants described in the invention include cropslike corn, rice, wheat, barley, rye, sorghum, cotton, soybean, peanuts,buck wheat, sugar beet, rapeseed, sun flower, sugar cane, and tobacco;vegetable like vegetables of Solanaceae (eggplant, tomato, bell pepper,pepper, potato, etc.), vegetables of Cucurbitaceae (cucumber, pumpkin,zucchini, water melon, melon, etc.), vegetables of Cruciferae (daikon,turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard,broccoli, cauliflower, etc.), vegetables of Compositae (burdock, crowndaisy, artichoke, lettuce, etc.), vegetables of Liliaceae (scallion,onion, garlic, asparagus, etc.), vegetables of Apiaccae (carrot,parsley, celery, parsnip, etc.), vegetables of Chenopodiaceae (spinach,leaf beet, etc.), vegetables of Lamiaccae (beefsteak plant, mint, basil,etc.), vegetables like strawberry, sweet potato, yam, and taro; kernelfruits (apple, western pear, Japanese pear, Chinese quince, quince,etc.), stone fruits (peach, plum, nectarine, Japanese apricot, cherry,apricot, prune, etc.), mandarins (tangerine, orange, lemon, lime, grapefruits, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio,cashewnut, macadamia nut, etc.), berries (blueberry, cranberry,blackberry, raspberry, etc.), fruits like grape, persimmon, olive,loquat, banana, coffee, date, coconut, and oil nut, trees other thanfruit tree like tea, mulberry, roadside trees (ash tree, birch, Americanflowering dogwood, eucalyptus, gingko, lilac, maple tree, oak tree,poplar tree, redbud tree, liquidambar, sycamore, zelkova, Japanesearborvitae, Japanese fir, hemlock spruce, juniper, pine tree, spruce,yew, elm, a horse chestnut, etc.), coral, Buddist pine, cedar, Japanesecypress, croton, spindle tree, Photinia glabra, etc.; grasses like turf(turf, gold turf, etc.), Bermuda grasses (Cynodon dactylon, etc.),bentgrasses (creeping bentgrass, Agrostis alba L., Agrostis capillaries,etc.), bluegrasses (Kentucky bluegrass, Poa trivialis L., etc.), fescues(tall fescue, chewings fescue, Festuca rabra L., etc.), rye grasses(Lolium temulentum L., Lolium perenne L., etc.), orchard grass, timothy,etc.; oil crops like oil coconut, Jatropha curcas, etc.; flowers (rose,carnation, mum, prairie gentian, common gypsophila, gerbera, marigold,salvia, petunia, verbena, tulip, Chinese aster, Gentiana scabra var.buergeri, lily, pansy, cyclamen, orchid, lily of the valley, lavender,stock, cauliflower, primula, poincetia, gladiolus, cattleya, daisy,verbena, cymbidium, begonia, etc.); a foliage plant, etc., but theinvention is not limited thereto.

The agrohorticultural plant described in the invention includes a plantgiven with resistance to HPPD inhibitor like Isoxaflutole, ALS inhibitorlike Imazetaphyr and tifensulfuron methyl, EPSP synthase inhibitor likeglifosate, glutamine synthase inhibitor like glufosinate, acetyl CoAcarboxylase inhibitor like sethoxydim, PPO inhibitor like flumioxazin,and herbicides like bromoxinil, dicamba and 2,4-D according to classicbreeding method or genetic recombination method.

Examples of the “agrohorticultural plant” given with resistanceaccording to classic breeding include rapeseed, wheat, sun flower, rice,and corn that are resistant to imidazoloinone-based ALS inhibitor likeImazetaphyr, and they are already commercially available in the name ofClearfield <trade name>.

Similarly, there is soybean resistant to sulfonylurea-based ALSinhibitor like tifensulfuron metil as produced by classic breedingmethod, and it is already commercially available in the trade name ofSTS Soybean. Similarly, examples of the “agrohorticultural plant” givenwith resistance to an acetyl CoA carboxylase inhibitor like trione-oximebased or aryloxyphenoxy propionic acid-based herbicides according toclassic breeding include SR Corn. The horticultural plant given withresistance to acetyl CoA carboxylase is described in Proceedings of theNational Academy of Sciences of the United States of America (Proc.Natl. Acad. Sci. USA), Vol 87, pages 7175 to 7179 (1990), etc. Further,a mutant acetyl CoA carboxylase which is resistant to acetyl CoAcarboxylase inhibitor is reported in Weed Science Vol. 53, pages 728 to746 (2005), and by introducing a mutant gene of acetyl CoA carboxylaseto a plant by genetic recombination technique or by introducing mutationfor giving resistance to acetyl CoA carboxylase of crops, a plant whichis resistant to an acetyl CoA carboxylase inhibitor can be produced.Further, by having site-specific amino acid substitution mutation on agene of crops based on introduction of a nucleic acid with basesubstitution mutation to a plant cell as represented by chimeraplastytechnique (Gura T. 1999. Repairing the Genome's Spelling Mistakes.Science 285: 316-318), a plant which is resistant to acetyl CoAcarboxylase inhibitor/herbicides can be produced.

Examples of the “agrohorticultural plant” given with resistanceaccording to genetic recombination technique include corn, soybean,cotton, rapeseed, and sugar beet that are resistant to glyfosate, andthey are already commercially available in the name of RoundupReady<trade name>, AgrisureGT, etc. Similarly, there are corn, soybean,cotton, and rapeseed varieties that are produced to be resistant toglufosinate by genetic recombination technique, and they are alreadycommercially available in the name of LibertyLink <trade name>, etc.Similarly, cotton having resistance to bromoxinil is also made availableby genetic recombination technique and is already commercially availablein the trade name of BXN.

The “agrohorticultural plant” includes a plant which is engineered bygenetic recombination technique to synthesize a selective toxin likeBacillus spp., for example.

Examples of the insecticidal toxin expressed in a genetically engineeredplant include an insecticidal protein originating from Bacillus cereusor Bacillus popilliae; 6-endotoxin originating from Bacillusthuringiensis like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1, and Cry9C, and insecticidal proteins like VIP1, VIP2, VIP3, andVIP3A; insecticidal proteins originating from a nematode;animal-produced toxins like scorpion toxin, spider toxin, bee toxin, andinsect specific neurotoxin; filamentous fungus toxin; plant lectin;agglutinin; protease like trypsin inhibitor, serine protease, patatin,cistatin, and papain inhibitor; ribosome inactivating proteins (RIP)like lysine, corn-RIP, abrin, saporin, and briodin; enzymes for steroidmetabolism like 3-hydroxysteroid oxidase, ccdisteroid-UDP-glycosyltransferase, and cholesterol oxidase; eedysone inhibitor; HMG-CoAreductase; ion channel inhibitors like sodium channel inhibitor andpotassium channel inhibitor, juvenile hormone esterase; natriuretichormone receptor; stilbene synthase; bibenzyl synthase; chitinase; andglucanase.

Examples of the toxins expressed in a genetically engineered plantinclude a hybrid toxin, a partially deleted toxin, and a modified toxinof an insecticidal protein like δ-endotoxin including Cry1Ab, Cry1Ac,Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, and Cry9C, and insecticidalproteins including VIP1, VIP2, VIP3, and VIP3A. The hybrid toxin isproduced by new combination of domains having different proteins basedon recombination technique. Examples of the partially deleted toxininclude Cry1Ab in which part of amino acid sequence is deleted. In themodified toxin, one or more amino acids of a natural type toxin arereplaced with other amino acids.

Examples of the toxins and recombinant plants capable of producing thetoxins are described in EP-A-0374753, WO93/07278, WO95/34656,EP-A-0427529, EP-A-451878, and WO03/052073, and the like.

The toxins contained in such recombinant plant can provide a plant witha resistance to harmful insects of Coleoptera, harmful insects ofDiptera, and harmful insects of Lepidoptera.

A genetically engineered plant which contains one or more pesticidalharmful insect-resistant gene and expresses one or more toxins is known,and some are already commercially available. Examples of the geneticallyengineered plant include YieldGard <trade name> (corn variety whichexpresses Cry1Ab toxin), YieldGard Rootworm <trade name> (corn varietywhich expresses Cry3Bb1 toxin), YieldGard Plus <trade name> (cornvariety which expresses Cry1Ab and Cry3Bb1 toxin), Herculex I <tradename> (corn variety which expresses phosphinotricine N-acetyltransferase (PAT) to give resistance to Cry1Fa2 toxin and glufosinate),NuCOTN33B <trade name> (cotton variety which expresses Cry1Ac toxin),Bollgard I <trade name> (cotton variety which expresses Cry1Ac toxin),Bollgard II <trade name> (cotton variety which expresses Cry1Ac andCry2Ab toxin), VIPCOT <trade name> (cotton variety which expresses VIPtoxin), NewLeaf <trade name> (potato variety which expresses Cry3Atoxin), NatureGard <trade name> Agrisure <trade name>GT Advantage (GA21glyfosate resistant trait), Agrisure <trade name> CB Advantage (Bt11Corn Borer (CB) trait), and Protecta <trade name>.

The “agrohorticultural plant” includes a plant which is geneticallyengineered to have an ability of producing an anti-pathogenic substancehaving selective activity.

Examples of the anti-pathogenic substance include PR proteins (PRPs,described in EP-A-0392225); ion channel inhibitors like sodium channelinhibitor and calcium channel inhibitor (KP1, KP4, KP6 toxin that areproduced by virus are known); stilbene synthase; bibenzyl synthase;chitinase; glucanase; and a substance produced by a microorganism likepeptide antibiotics, antibiotics having heterocycle, and a proteinfactor related to resistance to plant disease (referred to as “plantdisease resistant gene”, and described in WO03/000906). Suchanti-pathogenic substances and plants genetically engineered to producethe substances are described in EP-A-0392225, WO95/33818, andEP-A-0353191, etc.

The “agrohorticultural plant” includes a plant which is given withuseful traits like a trait of having modified oil components or a traitfor producing enhanced amount of amino acid according to geneticrecombination technique. Examples thereof include VISTIVE <trade name>(low-linolenic soybean having reduced linolen content) or high-lysine(high oil) corn (corn having enhanced amount of lysine or oil).

Further, there is also a stack variety in which multiple traits ofclassic herbicidal trait or herbicides-resistant gene, pesticidalinsect-resistant gene, anti-pathogenic substance-producing gene, anduseful traits like a trait of having modified oil components or a traitfor producing enhanced amount of amino acid are combined.

The agrochemical composition of the invention contains the triazinederivative of the invention or a salt thereof, and an agriculturallyacceptable carrier. The agrochemical composition of the invention maycontain additive components that may be normally employed foragrochemical formulations, as needed.

Examples of the additive components include carriers such as solidcarrier and liquid carrier, surface active agent, binder, tackifier,thickener, coloring agent, spreader, sticker, antifreezing agent,anticaking agent, collapsing agent, decomposition inhibitor and thelike.

If necessary, an antiseptic agent, a piece of plant (soybean powder,tobacco powder, walnut powder, wheat powder, wood powder, hulls, wheathulls, outer hulls, sawdust, pulp flock, corn stalk, nut shell, fruitcore chips, etc.) and the like may also be employed as additivecomponents.

These additive components may be used alone or in combination of two ormore kinds.

The above additive components will be described.

Examples of the solid carrier include natural minerals such as quartz,clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay,attapulgite, zeolite and diatomite; inorganic salts such as calciumcarbonate, ammonium sulfate, sodium sulfate and potassium chloride;organic solid carriers such as synthetic silicic acid, syntheticsilicate, starch, cellulose and plant powder, plastic carriers such aspolyethylene, polypropylene and polyvinylidene chloride; and the like.These may be used alone or in combination of two or more kinds.

Examples of the liquid carrier include alcohols classified broadly intomonohydric alcohols such as methanol, ethanol, propanol, isopropanol andbutanol, and polyhydric alcohols such as ethylene glycol, diethyleneglycol, propylene glycol, hexylene glycol, polyethylene glycol,polypropylene glycol and glycerin; polyhydric alcohol derivatives suchas propylene based glycol ether, ketones such as acetone, methylethylketone, methylisobutyl ketone, diisobutyl ketone, and cyclohexanone;ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether andtetrahydrofuran; aliphatic hydrocarbons such as n-paraffin, naphthene,isoparaffin, kerosene and mineral oil; aromatic hydrocarbons such asbenzene, toluene, xylene, solvent naphtha and alkylnaphthalene;halogenated hydrocarbons such as dichloroethane, chloroform and carbontetrachloride; esters such as ethyl acetate, diisopropyl phthalate,dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones suchas γ-butyrolactone; amides such as N,N-dimethylformamide,N,N-diethylformamide, N,N-dimethylacetamide and N-alkyl pyrrolidinone;nitriles such as acetonitrile; sulfur compounds such asdimethylsulfoxide; vegetable oils such as soybean oil, canola oil,cottonseed oil and castor oil; water; and the like. These may be usealone or in combination of two or more kinds.

The surface active agent is not particularly limited, but preferred arethose either turning into a gel in water or exhibiting swellingproperty. Examples thereof include non-ionic surface active agents suchas sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester,sucrose fatty acid ester, polyoxyethylene fatty acid ester,polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester,polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether,polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl etherformaldehyde condensate, polyoxyethylene polyoxypropylene block polymer,alkylpolyoxyethylene polypropylene block polymer ether, polyoxyethylenealkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acidbisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylenestyrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylenediol, polyoxyethylene ether silicone, ester silicone, fluorine-basedsurface active agent, polyoxyethylene castor oil, and polyoxyethylenehydrogenated castor oil; anionic surface active agents such as alkylsulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylenealkylphenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate,alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate,naphthalene sulfonate, alkyl naphthalene sulfonate, naphthalenesulfonicacid formaldehyde condensate salt, alkylnaphthalenesulfonic acidformaldehyde condensate salt, fatty acid salt, polycarboxylate,N-methyl-fatty acid sarcosinate, resin acid salt, polyoxyethylene alkylether phosphate, and polyoxyethylene alkylphenyl ether phosphate;cationic surface active agents such as laurylamine hydrochloride,stearylamine hydrochloride, oleylamine hydrochloride, stearylamineacetate, stearylaminopropylamine acetate, alkyltrimethylammoniumchloride, and alkyldimnethylbenzalkonium chloride; amino acid or betainetype amphoteric surface active agents; and the like.

These surface active agents may be used alone or in combination of twoor more kinds.

Examples of the binder or tackifier include carboxymethyl cellulose anda salt thereof, dextrin, water-soluble starch, xanthan gum, guar gum,sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinylacetate, sodium polyacrylate, polyethylene glycol having an averagemolecular weight of 6,000 to 20,000, polyethylene oxide having anaverage molecular weight of 100,000 to 5,000,000 natural phospholipids(for instance, cephalic acid, lecithin) and the like. Examples of thethickener include water-soluble polymers such as xanthan gum, guar gum,carboxymethyl cellulose, polyvinylpyrrolidone, carboxy vinyl polymer,acrylic polymer, starch derivative and polysaccharide; fine inorganicpowders such as high purity bentonite and white carbon; and the like.

Examples of the coloring agent include inorganic pigments such as ironoxide, titanium oxide and Prussian blue; organic dyes such as alizarindye, azo dye and metal phthalocyanine dye; and the like.

Examples of the extender agent include silicone surface active agent,cellulose powder, dextrin, processed starch, polyaminocarboxylic acidchelate compound, crosslinked polyvinylpyrrolidone, maleicacid-styrenes-methacrylic acid copolymer, half ester of polyhydricalcohol polymer with dicarboxylic anhydride, water-soluble salt ofpolystyrene sulfonate and the like.

Examples of the spreader include various surface active agents such asdialkyl sodium sulfosuccinate, polyoxyethylene alkyl ether,polyoxyethylene alkylphenyl ether and polyoxyethylene fatty acid ester,paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax,polyvinylalkyl ether, alkylphenol-formaldehyde condensate, syntheticresin emulsion and the like.

Examples of the antifreezing agent include polyhydric alcohols such asethylene glycol, diethylene glycol, propylene glycol, glycerin, and thelike.

Examples of the anticaking agent include polysaccharides such as starch,alginic acid, mannose and galactose, polyvinylpyrrolidone, white carbon,ester gum, petroleum resin and the like.

Examples of the collapsing agent include sodium tripolyphosphate, sodiumhexametaphosphate, metal stearate, cellulose powder, dextrin, copolymerof methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylicchelate compound, sulfonated styrene-isobutylene-maleic anhydridecopolymer, starch-polyacrylonitrile graft copolymer and the like.

Examples of the decomposition inhibitor include desiccants such aszeolite, quicklime and magnesium oxide; antioxidants that are based onphenol, amine, sulfur and phosphoric acid; ultraviolet absorbers thatare based on salicylic acid, benzophenone or the like; and the like.

Examples of the antiseptic agent include potassium sorbate,1,2-benzthiazolin-3-one and the like.

According to the agrochemical composition of the invention, in the casewhere the additive components described above are included, the contentratio of the carrier (weight base) is generally selected from 5 to 95%,preferably from 20 to 90%, the content ratio of the surface active agentis generally selected from 0.1 to 30%, preferably from 0.5 to 10%, andthe content ratio of other additives are selected from 0.1 to 30%,preferably from 0.5 to 10%.

The agrochemical composition of the invention can be used in any formssuch as liquid formulation, emulsifiable concentrate, wettable powder,dust, oil solution, water dispersible granule, flowable, granule, Jumboformulation, and suspoemulsion.

On the occasion of use, the agrochemical composition can be sprayedafter being diluted in an adequate concentration or be used directly.

The agrochemical composition of the invention can be used for foliageapplication, soil application, water-surface application or the like.The agrochemical composition of the invention, in particular theherbicides, is used for soils, i.e., farmland of fields and paddy fieldsin which agrohorticultural plants are cultivated.

For the agrochemical composition of the invention, the blending ratio ofactive component according to the invention is arbitrarily selected asneeded. In the case of dust, granule or the like, the ratio should bearbitrarily selected from 0.01 to 10% (by weight), preferably from 0.05to 5% (by weight). In the case of emulsifiable concentrate, wettablepowder or the like, the ratio should be arbitrarily selected from 1 to50% (by weight), preferably from 5 to 30% (by weight). In addition, inthe case of a flowable agent or the like, the ratio should bearbitrarily selected from 1 to 40% (by weight), preferably from 5 to 30%(by weight).

The application amount of the agrochemical composition according to theinvention varies depending on a kind of a compound to be used, targetweed, growth pattern, environmental conditions, formulation for use orthe like. In the case of a direct use of dust, granule or the like, theamount should be arbitrarily selected from 1 g to 50 kg, preferably from10 g to 10 kg per hectare as an active component. Further, in the caseof using in a liquid form, for example, in the case of emulsifiableconcentrate, wettable powder, flowable agent or the like, the amountshould be arbitrarily selected from 0.1 to 50,000 ppm, preferably from10 to 10,000 ppm.

The agrochemical composition of the invention has an excellentherbicidal activity, and therefore is useful as herbicides inparticular.

According to purpose of use, the agrochemical composition of theinvention may be formulated, mixed or used in combination with at leastone additional agrochemically active component, for example, a plantdisease control component, a pesticidal component, an acaricidalcomponent, an nematocidal component, a synergistic agent component, anattracting component, a repellent component, a herbicidal component, asafener component, a microbial pesticidal component, a plant growthcontrol component, a fertilizer component, a soil improving agent, etc.

When the composition is used in combination with other agrochemicallyactive component or fertilizer, the preparation of each individualcomponent may be mixed with others at the time of use. Further, eachpreparation of an individual component may be used in order, or usedwith an interval of some days. When the preparations are used with aninterval of some days, they may be applied with an interval of 1 day to40 days, for example, although it may vary depending on each componentto be used.

According to the agrochemical composition of the invention, when amixture of at least one compound selected from the triazine derivativesrepresented by Formula 1 and their salt and at least one kind selectedfrom other agrochemically active components is used, they are generallyused in weight ratio of 100:1 to 1:100, preferably 20:1 to 1:20, andparticularly 10:1 to 1:10.

Among other agrochemically active components that may be mixed or usedin combination with the compound of the invention in the agrochemicalcomposition of the invention, examples of known herbicides or plantgrowth control agents are described below, but the invention is notlimited thereto.

[Herbicides]

A1. Acetyl CoA Carboxylase (ACCase) Inhibition Type Herbicides

(A1-1) Aryl oxy phenoxy propionic acid-based compound:clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl,diclofop-P-methyl, fenoxaprop-P-ethyl, fluazifop-butyl,fluazifop-P-butyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, metamifop,propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl,quizalofop-P-tefuryl, and fenthiaprop-ethyl

(A1-2) Cyclohexane dione-based compound: alloxydim, butroxydim,clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, andtralkoxydim

(A1-3) Phenyl pyrazoline-based compound: aminopyralid, and pinoxaden

B. Acetolactate Synthase (ALS) Inhibition Type Herbicides

(B-1) Imidazolinone-based compound: imazamethabenz-methyl, imazamox,imazapic (including salts with amine or the like), imazapyr (includingsalts with isopropylamine or the like), imazaquin, and imazethapyr

(B-2) Pyrimidinyloxy benzoic acid-based compound: bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, andpyrimisulfan

(B-3) Sulfonylamino carbonyl triazolinone-based compound:flucarbazone-sodium, thiencarbazone (including sodium salt, methylester, or the like), propoxycarbazone-sodium, procarbazone-sodium

(B-4) Sulfonylurea-based compound: amidosulfuron, azimsulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl,imazosulfuron, iodosulfulon-methyl-sodium, mesosulfuron-methyl,metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl,prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl,trifloxysulfuron-sodium, triflusulfuron-methyl, tritosulfuron,orthosulfamuron, propyrisulfuron, metazosulfuron, and flucetosulfuron

(B-5) Triazolopyrimidine-based compound: cloransulam-methyi, diclosulam,florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam, andHNPC-C-9908 (code number)

C1. Herbicides 1 for Photosystem II Photosynthesis Inhibition

(C1-1) Phenylcarbamate-based compound: desmedipham and phenmedipham

(C1-2) Pyridazinone-based compound: chloridazon and brompyrazon

(C1-3) Triazine-based compound: ametryn, atrazine, cyanazine,desmetryne, dimethametryn, eglinazine-ethyl, prometon, prometryn,propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn,and trietazine

(C1-4) Triazinone-based compound: metamitron and metribuzin

(C1-5) Triazolinone-based compound: amicarbazone

(C1-6) Uracil-based compound: bromacil, lenacil, and terbacil

C2. Herbicides 2 for photosystem II photosynthesis inhibition

(C2-1) Amide-based compound: pentanochlor and propanil

(C2-2) Urea-based compound: chlorbromuron, chlorotoluron, chloroxuron,dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon,isouron, linuron, methabenzthiazuron, metobromuron, metoxuron,monolinuron, neburon, siduron, tebuthiuron, and metobenzuron

C3. Herbicides 3 for photosystem II photosynthesis inhibition

(C3-1) Benzothiadiazone-based compound: bentazone

(C3-2) Nitrile-based compound: bromofenoxim, bromoxynil (including esterform with butyric acid, octanoic acid and heptanoic acid), and ioxynil

(C3-3) Phenyl pyrazine-based herbicide compound: pyridafol, and pyridate

D. Photosystem 1 Radical Generation Type Herbicides

(D-1) Bipyridinium-based compound: diquat and paraquat dichloride

E. Protoporpyrinogen Oxidase (PPO) Inhibition Herbicides

(E-1) Diphenyl ether-based compound: acifluorfen-sodium, bifenox,chlomethoxyfen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fomesafen,lactofen, and oxyfluorfen

(E-2) N-Phenylphthalimide-based compound: cinidon-ethyl,flumiclorac-pentyl, flumioxazin, and chlorphthalim

(E-3) Oxy diazole-based compound: oxadiargyl and oxadiazon

(E-4) Oxazolidinedione-based compound: pentoxazone

(E-5) Phenylpyrazole-based compound: fluazolate and pyraflufen-ethyl

(E-6) Pyrimidinedione-based compound: benzfendizone, butafenacil, andsaflufenacil

(E-7) Thiadiazole-based compound: fluthiacet-methyl and thidiazimin

(E-8) Triazolinone-based compound: azafenidin, carfentrazone-ethyl,sulfentrazone, and bencarbazone

(E-9) Other compounds: flufenpyr-ethyl, profluazol, pyraclonil, SYP-298(code number), and SYP-300 (code number)

F1. Phytoene Desaturase (PDS) Inhibition Herbicides

(F1-1) Pyridazinone-based compound: norflurazon

(F1-2) Pyrimidine carboxamide-based compound: diflufenican andpicolinafen

(F1-3) Other compounds: beflubutamid, fluridone, flurochloridone, andflurtamone

F2. 4-Hydroxyphenylpyruvate Deoxygenase (HPPD) Inhibition Herbicides

(F2-1) Callistemon-based compound: mesotrione

(F2-2) Isoxazole-based compound: pyrasulfotale, isoxaflutnle, andisoxachlortole

(F2-3) Pyrazole-based compound: benzofenap, pyrazolynate, andpyrazoxyfen

(F2-4) Triketone-based compound: sulcotrione, tefuryltrion, tembotrione,pyrasulfotole, topramezone, bicyclopyrone, and4-chloro-5-(1,3-dioxocyclohexa-2-yl)carbonyl-2,3-dihydrobenzothiophene-1,1-dioxide

F3. Carotenoid Biosynthesis Inhibition (Unknown Target) Herbicides

(F3-1) Diphenyl ether-based compound: aclonifen

(F3-2) Isoxazolidinone-based compound: clomazone

(F3-3) Triazole-based compound: amitrole

G. EPSP Synthase Synthesis Inhibition (Aromatic Amino Acid BiosynthesisInhibition) Type Herbicides

(G-1) Glycine-based compound: glyphosate (including salts with sodium,amine, propylamine, isopropylamine, dimethylamine, and trimesium)

H. Glutamine Synthesis Inhibition Herbicides

(H-1) Phosphinic acid-based compound: bilanafos, glufosinate (includingsalts with amine or sodium)

I. Dihydropteroic Acid (DHP) Inhibition Herbicides

(I-1) Carbamate-based compound: asulam

K1. Microtubule Association Inhibition Type Herbicides

(K1-1) Benzamide-based compound: propyzamide and tebutam

(K1-2) Benzoic acid-based compound: chlorthal-dimethyl

(K1-3) Dinitroaniline-based compound: benfluralin, butralin,dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine, and trifluralin

(K1-4) Phosphoroamidate-based compound: amiprofos-methyl and butamifos

(K1-5) Pyridine-based compound: dithiopyr and thiazopyr

K2. Mitosis/Microtubule Tissue Formation Inhibition Herbicides

(K2-1) Carbamate-based compound: carbetamide, chlorpropham, propham,swep, and karbutilate

K3. Very long-chain fatty acid (VLCFA) synthase inhibition herbicides

(K3-1) Acetamide-based compound: diphenamid, napropamide, andnaproanilide

(K3-2) Chloroacetamide-based compound: acetochlor, alachlor, butachlor,butenachlor, diethatyl-ethyl, dimethachlor, dimethenamid,dimethenamid-P, metazachlor, metolachlor, pethoxamid, pretilachlor,propachlor, propisochlor, S-metolachlor, and thenylchlor

(K3-3) Oxyacetamide-based compound: flufenacet and mefenacet

(K3-4) Tetrazolinone-based compound: fentrazamide

(K3-5) Other compounds: anilofos, bromobutide, cafenstrole, indanofan,piperophos, fenoxasulfone, pyroxasulfone, and ipfencarbazone

L. Cellulose Synthesis Inhibition Herbicides

(L-1) Benzamide-based compound: isoxaben

(L-2) Nitrile-based compound: dichlobenil, chlorthiamid

(L-3) Triazolocarboxamide-based compound: flupoxame

M. Uncoupler (cell membrane distruction) type herbicides

(M-1) Dinitrophenol-based compound: dinoterb and DNOC (including saltswith amine or sodium)

N. Lipid Bioxynthesis (Excluding ACCase Inhibition) InhibitionHerbicides

(N-1) Benzofuran-based compound: benfuresate and ethofumesate

(N-2) Halogenated carboxylic acid-based compound: dalapon, flupropanate,and TCA (including salts with sodium, potassium, or ammonia)

(N-3) Phosphorodithioate-based compound: bensulide

(N-4) Thiocarbamate-based compound butylate, cycloate, dimepiperate,EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb,thiobencarb, tiocarbazil, tri-allate, and vernolate

O. Auxin Synthesis Inhibition Herbicides

(O-1) Benzoic acid-based compound: chloramben, 2,3,6-TBA, and dicamba(including salts with amine, diethyl amine, triethanolamine,isopropylamine, sodium, or lithium)

(O-2) Phenoxy carboxylic acid-based compound: 2,4,5-T, 2,4-D (includingsalts with amine, diethyl amine, isopropylamine, diglycolamine, sodium,or lithium), 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, MCPA,MCPA-thioethyl, MCPB (including sodium salt and ethyl ester), mecoprop(including salts with sodium, potassium, isopropylamine, triethanolamine, and dimethylamine), and mecoprop-P

(O-3) Pyridine carboxylic acid-based compound: clopyralid, fluroxypyr,picloram, triclopyr, and triclopyr-butotyl

(O-4) Quinoline carboxylic acid-based compound: quinclorac and quinmerac

(O-5) Other compounds: benazolin

P. Auxin Transport Inhibition Type Herbicides

(P-1) Phthalamates-based compound: naptalam (including salts withsodium)

(P-2) Semicarbazone-based compound: diflufenzopyr

Z. Herbicides with Unknown Mode of Action

Flamprop-M (including methyl, ethyl, and isopropyl ester), flamprop(including methyl, ethyl, and isopropyl ester), chlorflurenol-methyl,cinmethylin, cumyluron, daimuron, methyldymuron, difenzoquat,etobenzanid, fosamine, pyributicarb, oxaziclomefone, acrolcin,AE-F-150944 (code number), aminocyclopyrachlor, cyanamide,heptamaloxyloglucan, indaziflam, triaziflam, quinoclamine,endothal-disodium, phenisopham, BDPT, BAU-9403 (code number), SYN-523(code number, SYP-249 (code number), JS-913 (code number), IR-6396 (codenumber), metiozolin, Triafamone, HW-02 (code number), and BCS-AA10579(code number)

[Plant Growth Controlling Compounds]

1-Methylcyclopropene, 1-naphthylacetamide, 2,6-diisopropylnaphthalene,4-CPA, benzylaminopurine, ancymidol, aviglycine, carvone, chlormequat,cloprop, cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins,daminodide, dikegulac, dimethipin, ethephon, ethychlozate, flumetralin,flurenol, flurprimidol, forchlorfenuron, gibberellin acid, inabenfide,indol acetic acid, indol butyric acid, maleic hydrazide, mefluidide,mepiquat chloride, n-decanol, paclobutrazol, prohexadione-calcium,prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapac-ethyl,uniconazole, uniconazole-P, and ecolyst

Hereinbelow, known safeners which may be mixed or used in combinationwith the compound of the invention are exemplified, but the invention isnot limited thereto: benoxacor, furilazole, dichlormid, dicyclonone,DKA-24 (N1,N2-diallyl-N2-dichloroacetylglycinamide),AD-67(4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane), PPG-1292(2,2-dichloro-N-(1,3-dioxan-2-yl methyl)-N-(2-propenyl)acetamide),R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine),cloquintcet-mexyl, naphthalic anhydride (1,8-naphthalic anhydride),mefenpyr-diethyl, mefenpyr, mefenpyr-ethyl, fenchlorazole O ethyl,fenclorim, MG-191 (2-dichloromethyl-2-methyl-1,3-dioxane), cyometrinil,flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, mecoprop, MCPA,daimuron, 2,4-D, MON4660 (code number), oxabetrinil, cyprosulfamide,lower alkyl substituted benzoic acid, and TI-35 (code number).

Among other herbicidically active components that may be mixed or usedin combination with the compound of the invention, known plant diseasecontrol agents are described below, but the invention is not limitedthereto.

1. Nucleic Acid Biosynthesis Inhibitor

acyl alanine compound: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, andmetalaxyl-M;

oxazolidinone-based compound: oxadixyl;

butylol lactone-based compound: clozylacon and ofurace;

hydroxy-(2-amino)pyrimidine-based compound: bupirimate, dimethirimol,and ethirimol;

isoxazole-based compound: hymexazol;

isotahiazolone-based compound: octhilinone;

carboxylic acid-based compound: oxolinic acid

2. Mitosis and Cell Differentiation Inhibitor

benzimidazole-based compound: benomyl, carbendazim, fuberidazole, andthiabendazole;

thiophanate-based compound: thiophanate and thiophanate-methyl;

N-phenylcarbamate-based compound: diethofencarb;

toluamide-based compound: zoxamide;

phenylurea-based compound: pencycuron;

pyridinylmethyl benzamide-based compound: fluopicolide

3. Respiration Inhibitor

pyrimidine amine-based compound: diflumetorim;

carboxamide-based compound: benodanil, flutolanil, mepronil, fluopyram,fenfuram, carboxin, oxycarboxin, thifluzamide, bixafen, furametpyr,isopyrazam, penflufen, pcnthiopyrad, sedaxane, and boscalid;

methoxy acrylate-based compound: azoxystrobin, enestroburin,picoxystrobin, and pyraoxystrobin;

methoxycarbamate-based compound: pyraclostrobin, pyrametostrobin;

oxyiminoacetate compound: kresoxim-methyl and trifloxystrobin;

oxyiminoacetamide-based compound: dimoxystrobin, metominostrobin, andorysastrobin;

oxazolidinedione-based compound: famoxadone;

dihydrodioxadine-based compound: fluoxastrobin;

imidazolinone-based compound: fenamidone;

benzylcarbamate-based compound: pyribencarb;

cyanoimidazole-based compound: cyazofamid;

sulfamoyltriazole-based compound: amisulbrom;

dinitrophenylcrotonic acid-based compound: binapacryl, meptyldinocap,and dinocap;

2,6-dinitroaniline-based compound: fluazinam;

pyrimidinone hydrazone-based compound: ferimzone;

triphenyl tin-based compound: TPTA, TPTC, TPTH;

thiophenecarboxamide-based compound: silthiofam;

triazolopyrimidyl amine-based compound: ametoctradin

4. Amino Acid and Protein Synthesis Inhibitor

anilino pyrimidine-based compound: cyprodinil, mepanipyrim, andpyrimethanil;

enopyranuronic acid-based antibiotics: blasticidin-S and mildiomycin;

hexopyranosyl-based antibiotics: kasugamycin;

glucopyranosyl-based antibiotics: streptomycin;

tetracycline-based antibiotics: oxytetracycline;

other antibiotics: gentamycin

5. Preparation Acting on Signal Transduction Pathway

quinoline-based compound: quinoxyfen;

quinazoline-based compound: proquinazid;

phenylpyrrol-based compound: fenpiclonil and fludioxonil;

dicarboxyimide-based compound: chlozolinate, iprodione, procymidone, andvinclozolin

6. Lipid and Cell Membrane Synthesis Inhibitor

phosphorothiorate-based compound: edifenphos, iprobenfos, andpyrazophos;

dithiolane-based compound: isoprothiolane;

aromatic hydrocarbon-based compound: biphenyl, chloroneb, dicloran,quintozene, tecnazene, and tolclofos-methyl;

1,2,4-thiadiazole-based compound: etridiazole;

-   -   carbamate-based compound: iodocarb, propamocarb-hydrochloride,        and prothiocarb;

cinnamic amide-based compound: dimethomorph and flumorph;

valine amide carbamate-based compound: benthiavalicarb-isopropyl,iprovalicarb, and valifenalate;

mandelic amide-based compound: mandipropamid;

Bascillus subtilis and bactericidal lipopeptide product: Bacillussubtilis (strain: QST 713)

7. Sterol Biosynthesis Inhibitor

piperazine-based compound: triforine;

pyridine-based compound: pyrifenox;

pyrimidine-based compound: fenarimol and nuarimol;

imidazole-based compound: imazalil, oxpoconazole-fumarate, pefurazoate,prochloraz, and triflumizole;

triazole-based compound: azaconazole, bitertanol, bromuconazole,cyproconazole, difenoconazole, diniconazole, diniconazole-M,epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole,flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole,myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole,tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole,furconazole, furconazole-cis, and quinconazole;

morpholine-based compound: aldimorph, dodemorph, fenpropimorph, andtridemorph;

piperidine-based compound: fenpropidin and piperalin;

spiroketal amine-based compound: spiroxamine;

hydroxy anilide-based compound: fenhexamid;

thiocarbamate-based compound: pyributicarb;

aryl amine-based compound: naftifine and terbinafine

8. Glucan Biosynthesis Inhibitor

glucropyranosyl-based antibiotics: validamycin;

peptidyl pyridine nucleotide compound: polyoxin

9. Melanine Synthesis Inhibitor

isobenzofuranone-based compound: phthalide;

pyrroloquinoline-based compound: pyroquilon;

triazolobenzothiazole-based compound: tricyclazole;

carboxamide-based compound: carpropamid, diclocymet;

propionamide-based compound: fenoxanil

10. Preparation for Inducing Resistance to Plant Disease

benzothiadiazole-based compound: acibenzolar-S-methyl;

benzoisothiazole-based compound: probenazole;

thiadiazole carboxamide-based compound: tiadinil and isotianil;

natural product: laminarin

11. Preparation with Unknown Mode of Action or Multiple Mode of Action

copper compound: copper hydroxide, copper dioctanoate, copperoxychloride, copper sulfate, cuprous oxide, oxine-copper, Bordeauxmixture, and copper nonyl phenol sulphonate;

sulfur compound: sulfur;

dithiocarbamate-based compound: ferbam, mancozeb, maneb, metiram,propineb, thiram, zineb, ziram, and cufraneb;

phthalimide-based compound: captan, folpet, and captafol;

chloronitrile-based compound: chlorothalonil;

sulfamide-based compound: dichlofluanid, tolylfluanid;

guanidine-based compound: guazatine, iminoctadine-albesilate, andiminoctadine-triacetate, dodine;

other compounds: anilazine, dithianon, cymoxanil, vfosetyl (aluminum,calcium, and sodium), phosphorous acid and salts, tecloflalam,triazoxide, flusulfamide, diclomezine, methasulfocarb, ethaboxam,cyflufenamid, metrafenone, potassium bicarbonate, sodium bicarbonate,BAF-045 (code number), BAG-010 (code number), benthiazole, bronopol,carvone, chinomethionat, dazomet, DBEDC, debacarb, dichlorophcn,difenzoquat-methyl sulfate, dimethyl disulfide, diphenylamine,ethoxyquin, flumetover, fluoroimide, flutianil, fluxapyroxad,furancarboxylic acid, metam, nabam, natamycin, nitrapyrin,nitrothal-isopropyl, o-phenylphenol, oxazinylazole, oxyquinolinesulfate, phenazine oxide, polycarbamate, pyriofenone, S-2188 (codenumber), silver, SYP-Z-048 (code number), tebufloquin, tolnifanide,trichlamide, mineral oils, and organic oils

12. Microorganisms and Products of Microorganisms

Agrobacterium radiobacter, Fermented product from Aspergillus spp.,Bacillus spp., Harpin protein, Erwinia carotovora, Fusarium oxysporum,Gliocladium spp., Laccase, Pseudomonas spp., Talaromyces spp.,Trichoderma spp., Extract from mushroom, and Bacteriophage

Among other herbicidically active components that may be mixed or usedin combination with the compound of the invention, known pesticides,acaricides, nematocides, and synergistic agents are described below, butthe invention is not limited thereto.

[Pesticides, Acaricids & Nematocides]

1. Acetylcholine Esterase Inhibitor:

(1A) carbamate compound: alanycarb, aldicarb, aldoxycarb, bendiocarb,benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, 3,5-xylylmethylcarbamate (XMC), and xylylcarb

(1B) organo phosphorus compound: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diamidafos, diazinon, dichlorvos, dicrotophos,dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, DSP, EPN,ethion, cthoprophos, etrimfos, famphur, fenamiphos, fenitrothion,fenthion, fonofos, fosthiazate, fosthictan, heptenophos, isamidofos,isazophos, isofenphos-methyl, isopropyl O-(methoxyaminothio-phosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos,methidathion, mcvinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propaphos, propetamphos, pmthiofos, pyraclofos,pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, thionazin, triazophos, trichlorfon,vamidothion, dichlofenthion, imicyafos, isocarbophos, mesulfenfos, andflupyrazofos

2. GABA Receptor (Chloride Channel) Inhibitor

(2A) cyclodiene organic chloride-based compound: chlordane, endosulfan,and gamma-BCH

(2B) phenylpyrazole-based compound: acetoprol, ethiprole, fipronil,pyrafluprole, pyriprole, and RZI-02-003 (code number)

3. Preparation Acting on Sodium Channel

(3A) pyrethroid-based compound: acrinathrin, allethrin [includingd-cis-trans and d-trans], bifenthrin, bioallethrin, bioallcthrinS-cyclopentenyl, bioresmethrin, cycloprothrin, and cyfluthrin [includingbeta-], cyhalothrin [including gamma- and lambda-], cypermethrin[including alpha-, beta-, theta-, and zeta-], cyphenothrin [including(IR)-trans-isomers], deltamethrin, empenthrin, esfenvalerate,etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, andtau-fluvalinate [including tau-], halfenprox, imiprothrin, metofluthrin,permethrin, and phenothrin [including (1R)-trans-isomer], prallethrin,profluthrin, pyrethrine, resmethrin, RU15525 (code number), silafluofen,tefluthrin, tetramethrin, tralomethrin, transfluthrin, ZXI8901 (codenumber), fluvalinate, tetramethylfluthrin, and meperfluthrin

(3B) DDT-based compound: DDT, methoxychlor

4. Nicotinic Acetylchloine Receptor Agonist/Antagonist

(4A) neonicotinoid-based compound: acetamiprid, clothianidin,dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam

(4B) nicotine-based compound: nicotine-sulfate

5. Nicotinic Acetylchloine Receptor Allosteric Activator spinosyn-basedcompound: spinctoram and spinosad

6. Chloride Channel Activating Preparation

avermectin, milbemycin-based compound: abamectin, emamectin benzoate,lepimectin, milbemectin, ivermectin, and polynactins

7. Juvenile Hormone Preparation

diofenolan, hydroprene, kinoprene, methothrin, fenoxycarb, andpyriproxyfen

8. Preparation with Non-Specific Mode of Action (Multiple Mode ofAction)

1,3-dichloropropene, DCIP, ethylene dibromide, methyl bromide,chloropicrin, and sulfuryl fluoride

9. Feeding Inhibitor

pymetrozine, flonicamid and pyrifluquinazon

10. Mite Growth Controlling Agent

clofentezine, diflovidazin, hexythiazox, and etoxazole

11. Preparation for Disrupting Insect Intima

BT preparation:

12. ATP Biosynthesis Enzyme Inhibitor

diafenthiuron;

organo tin compound: azocyclotin, cyhexatin, and fenbutatin oxide;

propargite, tetradifon

13. Uncoupler

chlorfenapyr and DNOC

14. Preparation for Blocking Nicotinic Acetylchloine Channel

nereistoxin-based compound: bcnsultap, cartap, thiocyclam, andthiosultap

15. Chitin Biosynthesis Inhibitor (Type 0)

benzoylurea-based compound: bistrifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron, triflumuron, and fluazuron

16. Chitin Biosynthesis Inhibitor (Type 1)

buprofezin

17. Molting Inhibitor (for Diptera)

cyromazine

18. Ecdysone Agonist (for Promoting Molting)

diacylhydrazine-based compound: chromafenozide, halofenozide,methoxyfenozide, and tebufenozide

19. Octopamine Agonist

amitraz

20. Mitochondrial electron transport chain (complex III) inhibitor

cyflumetofen, hydramethylnon, acequinocyl, fluacrypyrim, andcycnopyrafen

21. Mitochondrial electron transport chain (complex 1) inhibitor

METI acaricides: fenazaquin, fenpyroximate, pyridabcn, pyrimidifen,tebufenpyrad, and tolfenpyrad

others: rotenone

22. Sodium Channel Inhibitor

indoxacarb and metaflumizon

23. Lipid Biosynthesis Inhibitor

tetronic-based insccticidcs/acaricides: spirodiclofen, spiromesifen, andspirotetramat

24. Mitochondrial Electron Transport Chain (Complex IV) Inhibitor

aluminium phosphide, phosphine, zine phosphide, calcium cyanide, andphosphinc

25. Neuronal Inhibitor Preparation (Unknown Mode of Action)

bifenazate

26. Aconitase Inhibitor

sodium fluoroacetate

27. Preparation Acting on Ryanodine Receptor

chlorantraniliprole, flubendiamide and cyantraniliprole

28. Other Preparations (Unknown Mode of Action)

azadirachtin, amidoflumct, bcnclothiaz, benzoximate, bromopropylate,chinomethionat, CL900167 (code number), cryolite, dicofol, dicyclanil,dienochlor, dinobuton, fenbutatin oxide, fenothiocarb, fluensulfone,flufencrim, flusulfamide, karanjin, metham, methoprene, methoxyfenozide,methyl isothiocyanate, pyridalyl, pyrifluquinazon, sulcofuron-sodium,sulflramid, and sulfoxaflor

29. Synergistic Agent

piperonyl butoxide and DEF.

Hereinafter, production methods of the compound of Formula 1 accordingto the compound of the invention, formulation examples, and applicationswill be described in detail with reference to Examples below. However,the invention is not limited to these Examples in any way. In thedescription below, “%” means “percent by weight” and “parts” means“parts by weight”.

Example 1 Production of 6-(2-hydroxy-6-oxocyclohexa-1-enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H,4H)-dione (Compound No. I-50) (1) Production of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride

0.93 g (3.76 mmol) of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid and 0.72 g (5.64 mmol) of oxalyl chloride were dissolved indichloromethane (20 ml). To the mixture, a drop of N,N-dimethylformamidewas added and stirred at room temperature for 2 hours. The reactionsolution was concentrated to obtain2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride as a pale yellow oily substance.

(2) Production 6-(2-hydroxy-6-oxocyclohexa-1-enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H,4H)-dione

0.63 g (5.64 mmol) of 1,3-cyclohexanedione and 0.57 g (5.64 mmol) oftriethylamine were dissolved in dichloromethane (20 ml) under icecooling. To the mixture, the dichloromethane solution (10 ml) of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride produced from the above (1) was slowly added dropwise, andstirred for 30 minutes under ice cooling. The reaction mixture wasextracted with chloroform, and the organic layer was washed with water,dried over magnesium sulfate, and concentrated under reduced pressure.The residues obtained were dissolved in acetonitrile (20 ml), added with0.57 g (5.64 mmol) of triethylamine and 0.03 g (0.38 mmol) of acetonecyanohydrin, and refluxed for 30 minutes under heating. Afterconcentration under reduced pressure, the residues were dissolved inwater and washed with ethyl acetate. The aqueous layer was acidified byusing citric acid, extracted with chloroform, dried over magnesiumsulfate, and concentrated under reduced pressure. The crystals obtainedwere washed with methanol to obtain 0.36 g of the target compound (yield28%).

Melting point: 182 to 185° C.

Example 2 Production of6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H,4H)-dione(Compound No. II-50)

1.50 g (6.07 mmol) of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid and 1.16 g (9.10 mmol) of oxalyl chloride were dissolved indichloromethane (30 ml). To the mixture, a drop of N,N-dimethylformamidewas added and stirred at room temperature for 2 hours. The reactionsolution was concentrated under reduced pressure to obtain2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride as a pale yellow oily substance.

Next, 1.22 g (9.10 mmol) of 1-methyl-5-hydroxypyrazole hydrochloride and1.53 g (15.17 mmol) of triethylamine were added to dichloromethane (30ml) under ice cooling. To the mixture, the dichloromethane solution (15ml) of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride was slowly added dropwise, and stirred for 30 minutes. Thereaction mixture was extracted with chloroform, and the organic layerwas washed with water, dried over magnesium sulfate, and concentratedunder reduced pressure. The residues obtained were dissolved inacetonitrile (30 ml), added with 0.92 g (9.10 mmol) of triethylamine and0.05 g (0.61 mmol) of acetone cyanohydrin, and refluxed for 30 minutesunder heating. The reaction mixture was concentrated under reducedpressure, and then the residues were dissolved in water and washed withethyl acetate. The aqueous layer was acidified by using citric acid,extracted with chloroform, dried over magnesium sulfate, andconcentrated under reduced pressure. The crystals obtained were washedwith methanol to obtain 0.40 g of the target compound (yield 20/).

Melting point: 197 to 199° C.

Example 3 Production of 6-(2-hydroxy-4-oxobicyclo[3.2.1]octa-2-en-ylcarbonyl]-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione (CompoundNo. III-50)

1.00 g (4.04 mmol) of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid and 1.03 g (8.09 mmol) of oxalyl chloride were dissolved indichloromethane (20 ml). To the mixture, a drop of N,N-dimethylformamidewas added and stirred at room temperature for 2 hours. The reactionsolution was concentrated under reduced pressure to obtain2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride as a pale yellow oily substance.

Next, 0.83 g (6.07 mmol) of bicyclo[3.2.1]octane-2,4-dione and 0.61 g(6.07 mmol) of triethylamine were dissolved in dichloromethane (20 mil)under ice cooling. To the solution, the dichloromethane solution (10 ml)of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonylchloride that is prepared previously was slowly added dropwise. Afterstirring for 30 minutes under ice cooling, the reaction mixture wasextracted with chloroform, and the organic layer was washed with water,dried over magnesium sulfate, and concentrated under reduced pressure.The residues obtained were dissolved in acetonitrile (20 ml), added with0.61 g (6.07 mmol) of triethylamine and 0.03 g (0.4 mmol) of acetonecyanohydrin, and refluxed for 30 minutes under heating. The reactionmixture was concentrated under reduced pressure, and then the residueswere dissolved in water and washed with ethyl acetate. The aqueous layerwas acidified by using citric acid, extracted with chloroform, driedover magnesium sulfate, and concentrated under reduced pressure. Thecrystals obtained were washed with methanol to obtain 0.70 g of thetarget compound (yield 47%).

Melting point: 163 to 165° C.

Example 4

Production of1-isopropyl-4-(2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-ylcarbonyl)-1H-pyrazole-5-yl propane-1-sulfonate (Compound No. II-267)

0.85 g (2.60 mmol) of 6-(5-hydroxy-1-isopropyl-1H-pyrazol-4-ylcarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione wasdissolved in 20 ml of dichloromethane. To the solution, 0.27 g (2.60mmol) of triethylamine and 0.37 g (2.60 mmol) of 1-propane sulfonylchloride were added at room temperature and stirred overnight. Thereaction mixture was concentrated under reduced pressure, and theresidues were purified by silica gel column chromatography (hexane:ethylacetate=1:1) to obtain 0.71 g of the target compound (yield 63%).

Melting point: 51 to 53° C.

Example 5 Production of2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-53) (1) Production of diethyl 2-(2-methylhydrazono)malonate

5.00 g (0.0287 mol) of diethyl ketomalonate was dissolved in 30 mlethanol. To the solution, 1.45 g (0.0316 mol) of methyl hydrazine wasadded and stirred for 7 hours at 60° C. followed by further stirringovernight at room temperature. The reaction mixture was concentratedunder reduced pressure and extracted with ethyl acetate. The organiclayer was washed with water, dried over magnesium sulfate, andconcentrated under reduced pressure. The resulting residues werepurified by silica gel column chromatography (hexane:ethyl acetate=1:1)to obtain 5.28 g of the target compound (yield 91%).

(2) Production of ethyl4-(4-chlorophenyl)-2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g(9.89 mmol) of DBU were dissolved in 50 ml of tetrahydrofuran. To thesolution, the tetrahydrofuran (10 mil) solution of 4-chlorophenylisocyanate (3.34 g, 21.7 mmol) was slowly added dropwise at roomtemperature, and stirred over night. The reaction mixture wasconcentrated under reduced pressure, and the residues were extractedwith ethyl acetate, washed with water, dried over magnesium sulfate, andconcentrated under reduced pressure. The resulting residues werepurified by silica gel column chromatography (hexane:ethyl acetate=7:1)to obtain 2.00 g of the target compound (yield 65%).

(3) Production of2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid

2.00 g (6.46 mmol) of ethyl2-methyl-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester was stirred at room temperature for 2 days in a mixed solventof acetic acid (30 ml) and cone. hydrochloric acid (30 ml). The reactionmixture was concentrated under reduced pressure to obtain 1.88 g of thetarget compound (yield, quantitative).

Melting point: 234 to 236° C.

Example 6 Production of2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-1) (1) Production of 2-methylsemicarbazide

13 g (282.1 mmol) of methyl hydrazine was dissolved in 60 ml oftetrahydrofuran. To the solution, 25 g (217 mmol) of trimethylsilylisocyanate was slowly added dropwise at 0° C. and further stirred for 1hour. To the reaction mixture, 40 ml of methanol was added and stirredfor 5 hours at 40° C. The reaction mixture was concentrated to obtain 18g of 2-methyl semicarbazide as a pale yellow solid (yield 93%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

3.15 (3H, s) 3.80 (2H, br), 5.61 (2H, br)

(2) Production of ethyl2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acidester

35.2 g (202 mmol) of diethyl ketomalonate and 18 g (202 mmol) of2-methyl semicarbazide were dissolved in 200 ml ethanol, and thenrefluxed under heating for 36 hours. The reaction solution wasconcentrated to obtain 31 g of ethyl2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acidester as a white solid (yield 78%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

1.39 (3H, t, J=7.1 Hz), 3.72 (3H, s), 4.42 (2H, q, 7.11 Hz), 938 (1H,br)

(3) Production of ethyl2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

2.0 g (10.0 mmol) of ethyl2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acidester, 1.9 g (13.5 mmol) of potassium carbonate, and 1.8 g (12.5 mmol)of methyl iodide were added to 20 ml of N,N-dimethylformamide, andstirred for 2 hours at 60° C. Upon the completion of the reaction, thereaction solution was added with water, and then extracted with ethylacetate. The organic layer obtained was dried over anhydrous magnesiumsulfate and concentrated to obtain 1.8 g of ethyl2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester (yield 86%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

1.40 (3H, t, J=7.1 Hz), 3.38 (3H, s), 3.74 (3H, s), 4.42 (2H, q, J=7.1Hz)

(4) Production of2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid 1.8 g (8.41 mmol) of ethyl

2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester was stirred at room temperature for 24 hours in a mixedsolvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). Thereaction solution was concentrated to obtain 1.40 g of2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid as a white solid (yield 90%).

Melting point: 220 to 223° C.

¹H-NMR (CDCl₃, TMS) δ(ppm):

3.48 (3H, s), 3.88 (3H, s)

Example 7 Production of2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-259) (1) Production of ethyl3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acidester

9.0 g (0.0517 mol) of diethyl ketomalonate and 7.81 g (0.0517 mol) of2-phenyl semicarbazide were stirred in 50 ml xylene for 1 hour at 100°C. The reaction mixture was refluxed under heating, and by adding sodiummethoxide (8.37 g, 0.155 mol) in small portions, the reaction wascompleted. After cooling to room temperature, the reaction mixture wasneutralized with 1 N aqueous hydrochloric acid solution, extracted withethyl acetate, and dried over magnesium sulfate. The reaction mixturewas concentrated under reduced pressure and the residues were isolatedand purified by silica gel column chromatography (hexane:ethylacetate=2:1) to obtain 6.18 g of the target compound (yield 46%).

(2) Production of ethyl2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

1.50 g (5.74 mmol) of ethyl3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acidester was dissolved in 30 ml of N,N-dimethylformamide, added with 60%sodium hydride (0.23 g, 5.74 mmol) under ice cooling, and furtherstirred for 30 minutes. The mixture was added with ethyl iodide (0.90 g,5.74 mmol) and stirred. After raising to room temperature, an aqueoussolution of ammonium chloride was added to terminate the reaction. Theresultant was extracted with diethyl ether, dried over magnesiumchloride, and concentrated under reduced pressure. The residues werepurified by silica gel column chromatography to obtain 1.33 g of thetarget compound (yield 80%).

(3) Production of2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid

1.30 g (4.49 mmol) of ethyl2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester was dissolved in 30 ml ethanol, added with a 25% aqueoussolution of sodium hydroxide (1.29 g 8.09 mmol), and stirred overnight.After dilution by adding water, the aqueous layer was washed withdiethyl ether. The aqueous layer was acidified by adding 6 N aqueoushydrochloric acid solution, and then extracted with ethyl acetate. Afterdrying over magnesium sulfate and concentration under reduced pressure,1.10 g of the target compound was obtained (yield 94%).

Example 8 Production of2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-265) (1) Production of ethyl2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g(9.89 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolvedin 50 ml of tetrahydrofuran. To the solution, the tetrahydrofuran (10ml) of methylisothiocyanate (1.58 g, 21.7 mmol) was slowly addeddropwise and stirred overnight. The reaction mixture was concentratedunder reduced pressure, extracted with ethyl acetate, washed with water,and dried over magnesium sulfate. The residues obtained afterconcentration under reduced pressure were purified by silica gel columnchromatography (hexane:ethyl acetate=3:1) to obtain 2.20 g of the targetcompound (yield 97%).

(2) Production of2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid 2.30 g (0.01 mol) of ethyl

2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester was stirred overnight at room temperature in a mixed solventof acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reactionmixture was concentrated under reduced pressure to obtain 2.01 g of thetarget compound (yield; quantitative).

Example 9 Production of2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-72) (1) Production of ethyl2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

2.0 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 3.3 g(21.8 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolvedin 20 ml of tetrahydrofuran. To the solution, 4.9 g (20.8 mmol) ofphenyl-2-cyanophenylcarbanate was added at room temperature and stirredfor 1 hour at the same temperature. After that, the mixture was refluxedunder heating for 3 hours. The reaction solution was concentrated andthe residues were extracted with ethyl acetate. The organic layerobtained was washed with water and an aqueous solution of citric acid inorder, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure. The residues were purified by silica gel columnchromatography (hexane:ethyl acetate 2:1) to obtain 2.3 g of ethyl2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester (yield 78%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

1.40 (3H, t, J=7.1 Hz), 3.81 (3H, s), 4.45 (2H, q, J=7.1 Hz), 7.39 (1H,d, J=8.0 Hz), 7.60-7.64 (1H, m), 7.75-7.80 (1H, m), 7.85 (1H, d, J=7.6Hz)

(2) Production of2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid 2.3 g (7.65 mmol) of ethyl

2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester was stirred for 24 hours at room temperature in a mixedsolvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). Thereaction solution was concentrated under reduced pressure to obtain 1.8g of2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid as a white solid (yield 90%).

Melting point: 213 to 215° C.

¹H-NMR (DMSO-d₆, TMS) δ(ppm):

3.65 (3H, s) 7.67 (1H, d, J=8.0 Hz) 7.70-7.75 (1H, m), 7.90-7.96 (1H,m),

8.09 (1H, d, J=7.4 Hz), 14.02 (1H, br)

Example 10 Production of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid (Compound No. V-50) (1) Production of ethyl2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester

2.0 g (9.89 mmol) of diethyl 2-oxomalonate and 0.04 g (0.2 mmol) ofp-toluene sulfonic acid were dissolved in 50 ml of toluene. To thesolution, 2.5 g (15.2 mmol) of 1-methyl-N-phenylhydrazine carboxamideswas added at room temperature, and then stirred for 2 hours with refluxunder heating. The reaction mixture was cooled to room temperature andadded with 0.08 g (0.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)followed by stirring at room temperature for two hours. The reactionsolution was washed with water and dried over magnesium sulfate. Thesolvent was distilled off to obtain ethyl2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester.

(2) Production of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid

Ethyl2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid ester produced from the above (1) was stirred for 24 hours at roomtemperature in a mixed solvent of acetic acid (30 ml) and conc.hydrochloric acid (30 ml). The reaction mixture was concentrated underreduced pressure, extracted with a saturated aqueous solution of sodiumhydrogen carbonate, washed with ethyl acetate, and then adjusted to beweakly acidic by using diluted hydrochloric acid. After that, themixture was extracted with ethyl acetate and dried over magnesiumsulfate, and the solvent was distilled off to obtain 2.6 g of2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylicacid as a white solid (2-step yield 70%).

Melting point: 195 to 198° C.

¹H-NMR (DMSO-d₆, TMS) δ(ppm):

3.59 (3H, s), 7.29-7.31 (2H, m), 7.43-7.54 (3H, m), 13.64 (1H, bs)

Physical property values (melting point or refractive index) of thecompound of the invention represented by Formula 1, which has beensynthesized according to the above Examples, are shown in Table 68 toTable 70 including above Examples. Herein, * means refractive index.

TABLE 68 Melting Point(° C.) or Compound No. Refractive Index(n_(D) ²⁰)I-2 87-89 I-3 1.5530* I-5 1.5630* I-9 1.5380* I-10 124-125 I-11 97-98I-14 126-129 I-16 116-118 I-19 132-134 I-27 1.5460* I-41 1.5495* I-43 98-101 I-47 155-157 I-50 182-185 I-51 184-185 I-52 187-190 I-53 182-183I-54 174-176 I-55 209-212 I-56 181-183 I-57 135-136 I-58 198-199 I-59190-193 I-60 190-191 I-61 186-187 I-62 137-139 I-63 166-169 I-64 89-92I-65 184-187 I-66 151-152 I-67 174-177 I-68 208-210 I-71 130-131 I-72166-169 I-73 181-184 I-74 108-111 I-75 173-176 I-76 242-245 I-77 192-194I-78 149-151 I-79 161-163 I-80  98-101 I-81 158-161 I-82 212-215 I-83191-194 I-84 124-127 I-85 235-238 I-86 199-202 I-87 197-198 I-88 160-163I-89 190-193 I-90 164-166 I-91 89-91 I-92 245-247 I-93 168-169 I-94155-157 I-96 151-153 I-98 155-157 I-99 178-181 I-105 186-188 I-106228-231 I-107 212-215 I-108 167-169 I-109 166-168 I-110 151-152 I-111196-199 I-115 144-147 I-116 176-179 I-117 140-143 I-118 140-143 I-119191-194 I-120 191-194 I-125 148-151 I-126 126-129 I-127 237-240 I-128217-220 I-129 155-158 I-131 204-205 I-134 215-217 I-135 152-154 I-136156-157 I-137 154-157 I-138 123-126 I-149 175-178 I-155 196-199 I-167183-186 I-169 178-180 I-170 213-215

TABLE 69 Melting Point(° C.) or Compound No. Refractive Index(n_(D) ²⁰)I-179 215-218 I-182 159-161 I-183 138-141 I-184 100-103 I-185 108-111I-187 180-183 I-189 190-193 I-198 135-137 I-199 169-170 I-202 161-162I-203 188-191 I-204 201-204 I-205 87-90 I-259 150-153 I-260 152-154I-261 190-193 I-262 103-106 I-263 174-176 I-265 164-167 I-268 201-204I-269 112-115 I-270 172-175 I-271 251-254 I-272 204-207 I-274 101-103I-275 89-92 I-276 167-170 I-277 96-99 I-278  98-101 I-279 218-220 I-280168-171 I-281 146-147 I-282 148-151 I-283 172-175 I-284 160-162 I-285149-152 I-286 88-91 I-287 155-158 I-288 94-97 I-289 215-218 I-290138-141 I-291 194-197 I-292 167-169 I-293 158-160 I-294 113-115 I-2951.5360* I-296 1.5300* I-297 89-92 I-298 148-150 I-299 212-215 I-300203-205 I-301 274-277 I-302 222-224 I-303 62-65 I-304 148-151 I-30758-61 I-328 58-61 I-463 131-134 I-464 168-170 I-465 211-213 I-466 89-92I-467 211-214 I-468 128-130 I-469 172-174 I-470 147-148 I-471 1.5620*I-472 162-164 I-473 143-146 I-474 70-73 I-475 83-86 I-476 191-193 I-477149-151 I-478 1.5270* I-479 1.5450* I-480 179-181 II-50 197-199 II-26751-53 III-50 163-165 III-62 158-159 VI-1 151-154 VI-5 145-148 VI-6145-146 VI-7 163-166 VI-65 93-96 VI-97 158-160

Compound number and ¹H-NMR data (standard; TMS, δ (ppm) value) are givenbelow.

Data without a name of solvent are measured by using CDCl₃.

Compound No. I-1:

2.04-2.10 (2H, m), 2.45-2.49 (2H, m), 2.76-2.80 (2H, m), 3.56 (3H, s)

3.65 (3H, s), 16.05 (1H, br)

Compound No. I-3:

0.92 (3H, t, J=6.00 Hz), 1.69 (2H, q, J=6.00 Hz), 2.03-2.11 (2H, m),

2.45-2.49 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.89 (2H, t, J=6.00Hz),

16.05 (1H, br)

Compound No. I-4:

1.49 (6H, d, J=6.00 Hz), 2.03-2.11 (2H, m), 2.44-2.49 (2H, m), 2.74-2.79(2H, m),

3.61 (3H, s), 5.07 (1H, sept, J=6.00 Hz), 16.08 (1H, br)

Compound No. I-5:

0.95 (3H, t, J=7.2 Hz), 1.32-1.43 (2H, m), 1.59-1.68 (2H, m), 2.03-2.10(2H, m),

2.45-2.49 (2H, m), 2.75-2.79 (2H n), 3.64 (3H, s), 3.92 (2H, t, J=6.9Hz), 16.05 (1H, br)

Compound No. I-9:

0.88 (3H, t, J=6.6 Hz), 1.20-1.40 (6H, m), 1.58-1.64 (2H, m), 2.03-2.12(2H, m),

2.44-2.48 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.89-3.94 (2H, m),

16.04 (1H, br)

Compound I-27:

1.65 (3H, t, J=3.00 Hz), 2.03-2.09 (2H, m), 2.31-2.36 (2H, m), 2.44-2.49(2H, m),

2.74-2.79 (2H, m), 3.64 (31H, s), 4.01 (2H, t, J=6.00), 16.00 (1H, br)

Compound No. I-41:

1.89-1.97 (2H, m), 2.04-2.11 (2H, m), 2.44-2.48 (2H, m), 3.31 (3H, s),

3.44 (2H, t, J=6.0 Hz), 3.64 (3H, s), 4.03 (2H, t, J=7.0 Hz), 16.04 (1H,br)

Compound No. I-75:

2.05-2.11 (2H, m), 2.45-2.49 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s),

7.05-7.09 (1H, m), 7.14-7.21 (1H, m), 7.24-7.33 (1H, m), 15.99 (1H, s)

Compound No. I-76:

2.04-2.09 (2H, m), 2.46-2.50 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s),

6.88-6.96 (3H, m), 15.97 (1H, s)

Compound No. I-77:

2.03-2.09 (2H, m), 2.45-2.49 (2H, m), 2.75-2.78 (2H, m), 3.71 (3H, s),

7.11-7.14 (1H, m), 7.18-7.33 (2H, m), 15.95 (1H, s)

Compound No. I-79:

2.04-2.10 (2H, m), 2.45-2.50 (2H, m), 2.75-2.79 (2H, m), 3.70 (3H, s),7.10-7.24 (3H, m), 15.96 (1H, s)

Compound No. I-80:

2.01-2.08 (2H, m), 2.46-2.49 (2H, m), 2.75-2.78 (2H, m), 3.71 (3H, s),7.05-7.08 (2H, m), 7.40-7.48 (1H, m), 15.93 (1H, s)

Compound No. I-81:

2.05-2.08 (2H, m), 2.45-2.50 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s),7.14-7.19 (1H, m), 7.43 (1H, d, J=2.5), 7.57 (1H, d, J=8.5), 15.97 (1H,s)

Compound No. I-295:

0.85-0.89 (3H, m), 1.26-1.32 (10H, m), 1.57-1.65 (2H, m), 2.05-2.12 (2H,m),

2.44-2.49 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.88-3.93 (2H, m),16.04 (1H, br)

Compound No. I-296:

0.85-0.90 (3H, m), 1.25-1.36 (14H, m), 1.59-1.69 (2H, m), 2.05-2.09 (2H,m), 2.44-2.49 (2H, m), 2.74-2.79 (2H, m), 3.64 (3H, s), 3.88-3.93 (2H,m), 16.04 (1H, br)

Compound No. I-306:

0.96 (3H, t, J=7.15), 1.39-1.46 (2H, m), 1.69-1.71 (2H, m), 2.05-2.09(2H, m), 2.44-2.48 (2H, m), 4.01 (2H, t, J=7.69), 7.32-7.36 (2H, m),7.56-7.59 (1H, m), 7.83-7.88 (1H, m), 8.61-8.63 (1H, m), 16.05 (1H, br)

Compound No. I-308:

0.88-0.92 (3H, m), 0.35-0.37 (4H, m), 0.79-1.82 (2H, m). 2.03-2.07 (2H,m),

2.44-2.49 (2H, m). 2.73-2.78 (2H, m), 4.01 (2H, t, J=7.69). 7.28-7.30(2H, m),

7.43-7.53 (3H, m), 16.06 (1H, br)

Compound No. I-339:

1.84-2.11 (4H, m), 2.44-2.48 (2H, m), 2.74-2.78 (2H, m), 3.64 (3H, s),

3.69-3.92 (3H, m), 4.07-4.34 (2H, m), 16.04 (1H, br)

Compound No. I-462:

1.30 (3H, t, J=7.66), 2.03-2.07 (2H, m). 2.45-2.49 (2H, m), 2.69-2.77(4H, m),

3.68 (3H, s), 7.28-7.30 (1H, m), 7.77-7.73 (1H, m). 8.51 (1H, s), 16.03(1H, br)

Physical property values of the production intermediate [13a] and [3b]are given in Table 70 and Table 71.

TABLE 70 Compound No. Melting Point (° C.) IV-116 111-114 IV-117 100-102IV-118 118-121 IV-136 131-133 IV-137 102-105 IV-138 122-125 IV-182107-108 IV-185 50-53 IV-197 122-125 IV-259 84-86 IV-260 107-109 IV-261132-135 IV-275 102-103 IV-276 46-49 IV-278 171-172 IV-280 137-140 IV-284136-137 IV-285 112-114 IV-287 140-142 IV-288 101-102 IV-290 124-127IV-291 137-138

TABLE 71 Compound No. Melting Point(° C.) V-1 220-223 V-2 165-168 V-3113-115 V-4 122-125 V-5  98-100 V-9  99-102 V-10 127-129 V-11 82-84 V-14142-144 V-16 155-158 V-27 114-117 V-41 90-91 V-43 145-146 V-47 144-147V-50 195-198 V-51 154-157 V-52 118-120 V-53 234-236 V-54 95-98 V-5595-98 V-56 212-215 V-57 150-152 V-58 196-199 V-60 145-146 V-61 173-174V-66 164-166 V-67 200-203 V-68 206-209 V-72 213-215 V-73 221-224 V-87162-165 V-88 227-230 V-89 184-186 V-90 156-159 V-91 179-181 V-92 207-210V-93 220-223 V-99 166-169 V-105 169-171 V-106 231-234 V-107 166-169V-108 153-156 V-109 197-198 V-110 194-197 V-111 187-190 V-115 188-191V-119 205-208 V-125 173-175 V-127 135-138 V-128 186-188 V-129 198-201V-131 201-204 V-135 224-227 V-149 216-218 V-155 229-231 V-167 211-212V-169 199-202 V-170 177-180 V-179 237-240 V-184 158-161 V-189 200-201V-202 200-203 V-203 164-167 V-204 199-202 V-268 201-204 V-269 155-157V-270 184-187 V-271 208-211 V-272 100-102 V-273 202-205 V-275 166-169V-282 193-196 V-283 186-189 V-291 175-178 V-294 204-207 V-295 105-107V-296 106-108 V-297 176-179 V-298 145-146 V-299 241-244 V-300 245-248V-301 259-261 V-302 211-212 V-303 152-155 V-304 140-143 V-305 166-167V-328 143-146 V-358 240-243 V-359 91-94 V-360 240-242 V-361 155-158V-362 148-151 V-363 189-192 V-364 213-216 V-365 75-78 V-366 218-221V-367 192-195 V-368 153-156 V-369 111-113 V-370 100-103 V-371 80-83

Compound number and ¹H-NMR data (standard; TMS, δ (ppm) value) for theproduction intermediates are given below. Data without a name of solventare measured by using CDCl₃.

Compound No. IV-19:

1.19-1.41 (3H, m), 1.39 (3H, t, J=5.3 Hz), 1.56-1.66 (3H, m), 1.83-1.87(2H, m),

2.37 (2H, dq, J=3.3 Hz, 12.1 Hz), 3.68 (3H, s), 4.41 (2H, q, J=7.1 Hz),

4.73 (1H, tt, J=3.3 Hz, 12.1 Hz)

Compound No. IV-50:

1.39 (3H, t, J=7.1 Hz), 3.71 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.24-7.26(2H, m), 7.49-7.57 (3H, m)

Compound No. IV-53:

1.39 (3H, t, J=5.3 Hz), 3.77 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.18 (2H,d, J=6.4 Hz),

7.49 (2H, d, J=6.4 Hz)

Compound No. IV-56:

1.39 (3H, t, J=7.1 Hz), 3.77 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.20-7.22(4H, m)

Compound No. IV-59:

1.39 (3H, t, J=7.1 Hz), 2.41 (3H, s), 3.77 (3H, s), 4.42 (2H, q, J=7.1Hz),

7.10 (2H, d, J=8.3 Hz), 7.31 (2H, d, J=8.3 Hz)

Compound No. IV-62:

1.39 (3H, t, J=7.1 Hz) 3.76 (3H, s), 3.84 (3H, s), 4.43 (2H, q, J=7.1Hz),

7.01 (2H, d, J=9.0 Hz), 7.14 (2H, d, J=9.0 Hz)

Compound No. IV-63:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.30 (1H,d, J=7.7 Hz),

7.67 (1H, t, J=7.7), 7.74 (1H, dt, J=1.1 Hz, 7.7 Hz), 7.84 (1H, dd,J=1.1 Hz, 7.7 Hz)

Compound No. IV-64:

1.40 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.44 (2H, q, J=7.1 Hz), 7.44 (1H,d, J=8.0 Hz),

7.54 (1H, s), 7.66 (1H, J=8.0 Hz), 7.75 (1H, d, J=8.0 Hz)

Compound No. IV-65:

1.40 (3H, t, J=5.3 Hz), 3.79 (3H, s), 4.44 (2H, q, J=5.3 Hz), 7.39 (2H,d, J=6.2 Hz),

7.79 (2H, d, J=6.2 Hz)

Compound No. IV-71:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.28 (2H,d, J=8.5 Hz),

7.36 (2H, d, J=8.5 Hz)

Compound No. IV-74:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.44 (2H, q, J=7.1 Hz),

7.39 (2H, dd, J=1.9 Hz, 6.6 Hz), 7.82 (2H, dd, J=1.9 Hz, 6.6 Hz)

Compound No. IV-78:

1.40 (3H, t, J=7.1 Hz), 3.79 (3H, s), 4.43 (2H, q, J=7.1 Hz), 6.99-7.05(2H, m),

7.22-7.28 (1H, m)

Compound No. IV-93:

1.39 (3H, t, J=7.1 Hz), 3.77 (3H, s), 3.78 (6H, s), 4.43 (2H, q, J=7.1Hz),

6.35 (2H, d, J=2.2 Hz), 6.55 (1H, J=2.2 Hz)

Compound No. IV-96:

1.39 (3H, t, J=7.1 Hz), 3.76 (6H, s), 3.83 (3H, s), 4.42 (2H, q, J=7.1Hz),

6.55-6.59 (2H, m), 7.05 (1H, d, J=9.1 Hz)

Compound No. IV-134:

1.40 (3H, t, J=5.3 Hz), 3.77 (3H, s), 3.79 (3H, s), 4.43 (2H, q, J=5.3Hz),

6.97 (1H, d, J=6.8 Hz), 7.17 (1H, d, J=2.0 Hz), 7.41 (1H, dd, J=2.0 Hz,6.8 Hz)

Compound No. IV-179:

1.39 (3H, t, J=5.3 Hz), 3.77 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.32 (1H,d, J=5.7 Hz),

7.46 (1H, dd, J=5.7 Hz, 3.7 Hz), 7.92 (1H, dt, J=1.1 Hz, 5.7 Hz),

8.68 (1H, dt, J=3.7 Hz, 1.1 Hz)

Compound No. IV-198:

1.40 (3H, t, J=5.3 Hz), 3.78 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.07-7.12(2H, m),

7.42 (1H, dd, J=1.1 Hz, 4.0 Hz)

Compound No. IV-259:

1.39 (3H, t, J=7.1 Hz), 1.43 (3H, t, J=7.1 Hz), 4.17 (2H, q, J=7.1 Hz),

4.43 (2H, q, J=7.1 Hz), 7.21-7.26 (2H, m), 7.44-7.55 (3H, m)

Compound No. IV-260:

1.39 (3H, t, J=7.1 Hz), 1.43 (6H, d, J=6.8 Hz), 4.42 (2H, q, J=7.1 Hz),

5.01 (1H, p, J=6.8 Hz), 7.22-7.26 (2H, m), 7.46-7.55 (3H, m)

Compound No. IV-261:

1.40 (3H, t, J=7.1 Hz), 4.46 (2H, q, J=7.1 Hz), 7.23-7.26 (2H, m),

7.47 (1H, t, J=57.8 Hz), 7.51-7.66 (3H, m)

Compound No. IV-262:

1.39 (3H, t, J=7.1 Hz), 4.44 (2H, q, J=7.1 Hz), 7.26-7.60 (10H, m)

Compound No. IV-265:

1.40 (3H, t, J=7.1 Hz), 3.71 (3H, s), 4.05 (3H, s), 4.44 (2H, q, J=7.1Hz)

Compound No. IV-286:

1.19-1.17 (6H, dd, J=7.0 Hz, J=2.2 Hz), 1.41-1.37 (3H, t, J=7.0 Hz),

2.65-2.58 (1H, sept., J=7.0 Hz), 3.78 (3H, s), 4.46-4.39 (2H, q, J=7.0Hz),

7.05-7.03 (1H, d, J=8.0 Hz), 7.33-7.29 (1H, m), 7.47-7.46 (2H, d, J=4.0Hz)

Compound No. V-19: (solvent for measurement: DMSO-d₆)

1.09-1.34 (3H, m), 1.59-1.64 (2H, m), 1.76-1.80 (2H, m),

2.22 (2H, dq, J=3.3 Hz, 12.3 Hz), 3.51 (3H, s), 4.54 (1H, tt, J=3.3 Hz,12.3 Hz),

13.53 (1H, bs)

Compound No. V-50: (solvent for measurement: DMSO-d₆)

3.59 (3H, s), 7.29-7.31 (2H, m), 7.43-7.54 (3H, m), 13.64 (1H, bs)

Compound No. V-53: (solvent for measurement: DMSO-d₆)

3.59 (3H, s), 7.35 (2H, J=1.6 Hz, 5.0 Hz), 7.59 (2H, dd, J=1.6 Hz, 5.0Hz),

13.66 (1H, bs)

Compound No. V-56: (solvent for measurement: DMSO-d₆)

3.59 (3H, s), 7.34-7.37 (4H, m), 13.65 (1H, bs)

Compound No. V-59: (solvent for measurement: DMSO-d₆)

2.36 (3H, s), 3.58 (3H, s), 7.17 (2H, d, J=8.3 Hz), 7.30 (2H, d, J=8.3Hz),

13.62 (1H, bs)

Compound No. V-62: (solvent for measurement: DMSO-d₆)

3.39 (3H, s), 3.74 (3H, s), 6.93 (2H, d, J=9.0), 7.39 (2H, d, J=9.0 Hz),

9.54 (1H, bs)

Compound No. V-63: (solvent for measurement: DMSO-d₆)

3.62 (3H, s), 7.64 (1H, d J=7.7 Hz), 7.75 (1H, t, J=7.68 Hz), 7.87-7.94(2H, m),

13.90 (1H, bs)

Compound No. V-64: (solvent for measurement: DMSO-d₆)

3.41 (3H, s) 7.46 (1H, d, J=6.0 Hz). 7.60 (1H, t, J=6.0 Hz), 7.82 (1H,d, J=6.0 Hz),

7.97 (1H, s), 9.90 (1H, bs)

Compound No. V-65: (solvent for measurement: DMSO-d₆)

3.60 (3H, s), 7.58 (2H, d, J=8.3 Hz), 7.92 (2H, d, J=8.3 Hz), 13.69 (1H,bs) [0259]

Compound No. V-71: (solvent for measurement: DMSO-d₆)

3.59 (3H, s), 7.47 (2H, dt, J=9.3 Hz, 2.2 Hz), 7.54 (2H, d, J=9.3 Hz),13.67 (1H, bs)

Compound No. V-75:

3.92 (3H, 7.03-7.06 (1H, m), 7.13-7.18 (1H, m), 7.35-7.41 (1H, m)

Compound No. V-76:

3.92 (3H, s), 7.85-7.87 (2H, m), 7.00-7.12 (1H, m)

Compound No. V-77:

3.94 (3H, s), 7.07-7.11 (1H, m), 7.29-7.31 (1H, m), 7.38-7.42 (1H, m)

Compound No. V-78: (solvent for measurement: DMSO-d₆)

3.61 (3H, s), 7.25-7.31 (1H, m), 7.49-7.58 (2H, m), 13.79 (1H, bs)

Compound No. V-79:

3.94 (3H, s), 7.05-7.07 (1H, m), 7.27-7.32 (2H, m)

Compound No. V-80:

3.94 (3H, s). 7.12-7.18 (2H, m), 7.52-7.61 (1H, m)

Compound No. V-81: (solvent for measurement: DMSO-d₆)

3.60 (3H, s), 7.69 (1H, s), 7.82 (1H, d, J=7.7 Hz)

Compound No. V-82:

3.92 (3H, s), 7.20 (2H, s), 7.56 (1H, s)

Compound No. V-83:

3.93 (3H, s), 7.25 (1H, d, J=10.4), 7.44 (1H, t, J=8.0), 7.68 (1H, d,J=11.7)

Compound No. V-84:

3.93 (3H, s), 7.21 (1H, d, J=15.6), 7.45-7.48 (1H, m), 7.68 (1H, d,J=2.4 Hz)

Compound No. V-85:

3.93 (3H, s), 7.33 (1H, d, J=5.7), 7.49-7.58 (2H, m)

Compound No, V-86:

3.95 (3H, s), 7.45-7.56 (2H, m)

Compound No. V-93: (solvent for measurement: DMSO-d₆)

3.58 (3H, s), 3.74 (6H, s), 7.52 (2H, d, J=2.2 Hz), 6.59 (1H, t, J=2.2Hz),

13.63 (1H, bs)

Compound No. V-96: (solvent for measurement: DMSO-d₆)

3.59 (3H, s), 3.73 (3H, s), 3.82 (3H, s), 7.62 (1H, dd, J=2.5 Hz, 8.8Hz),

6.71 (1H, s), 7.16 (1H, d, J=8.5 Hz), 13.76 (1H, bs)

Compound No. V-134: (solvent for measurement: DMSO-d₆)

3.60 (3H, s), 3.76 (3H, s), 7.23 (1H, d, J=9.1 Hz), 7.43 (1H, d, J=2.8Hz),

7.54 (1H, dd, J=2.8 Hz, 9.1 Hz), 13.84 (1H, bs)

Compound No. V-170: (solvent for measurement: DMSO-d₆)

3.58 (3H, s), 6.10 (2H, s), 6.78 (1H, dd, J=10 Hz, 6.2 Hz), 6.89 (1H, d,J=1.0 Hz),

7.01 (1H, d, J=6.2 Hz), 13.63 (1H, bs)

Compound No. V-179: (solvent for measurement DMSO-d₆)

3.60 (3H, s), 7.49 (1H, d, J=7.7 Hz), 7.55 (1H, ddd, J=1.1 Hz, 5.0 Hz,7.7 Hz),

8.05 (1H, dt, J=1.9 Hz, 7.7 Hz), 8.62 (1H, dd, J=1.1 Hz, 5.0 Hz)

Compound No. V-198: (solvent for measurement: DMSO-d₆)

3.57 (3H, s), 7.07-7.10 (2H, m), 7.63 (1H, J=1.9 Hz, 5.2 Hz)

Compound No. V-259: (solvent for measurement: DMSO-d₆)

1.09 (3H, t, J=5.3 Hz), 3.96 (2H, q, J=5.3 Hz), 7.32-7.37 (2H, m),

7.45-7.54 (3H, m), 9.51 (1H, bs)

Compound No. V-261: (solvent for measurement: DMSO-d₆)

7.36-7.53 (5H, m), 7.82 (1H, t, J=42.9 Hz)

Compound No. V-265: (solvent for measurement: DMSO-d₆)

3.53 (3H, s), 3.90 (3H, s)

Compound No. V-268: (solvent for measurement: DMSO-d₆)

1.45 (3H, t), 3.91 (3H, s), 4.09 (2H, q), 7.04 (2H, d), 7.15 (2H, d)[0261]

Formulation Example 1 Wettable Powder

10 parts of the compound (I-1), 0.5 parts of polyoxyethylene octylphenylether, 0.5 parts of sodium β-naphthalene sulfonate formalin condensate,20 parts of diatomaceous earth, and 69 parts of clay were mixed andpulverized to give a wettable powder

Formulation Example 2 Flowable Agent

20 parts of roughly crushed compound (I-1) were dispersed in 69 parts ofwater, and added with 200 ppm of silicone AF-118N (trade name,manufactured by Asahi Kasei Corporation) while simultaneously adding 4parts of polyoxyethylene styryl phenyl ether sulfonate and 7 parts ofethylene glycol. After mixing for 30 minutes by high-speed mixer, themixture was pulverized using a wet-type pulverizer to give a flowableagent.

Formulation Example 3 Emulsifiable Concentrate

30 parts of the compound (I-1), 60 parts of a mixture of xylene andisophorone (1:1 mixture), and 10 parts of a mixture of polyoxyethylenesorbitan alkylate, polyoxyethylene alkylaryl polymer, and alkylarylsulfonate were mixed well to give an emulsifiable concentrate.

Formulation Example 4 Granules

10 parts of the compound (I-1), 80 parts of extender in which talc andbentonite are mixed in ratio of 1 to 3, 5 parts of white carbon, and 5parts of a mixture of polyoxyethylene sorbitan alkylate, polyoxyethylenealkylaryl polymer, and alkylaryl sulfonate were added with 10 parts ofwater. After kneading well, the resulting paste was extruded through asieve (diameter; 0.7 mm) followed by drying. By cutting it to havelength of 0.5 to 1 mm, granules were obtained.

Effect of the compounds of the invention is explained by way offollowing test examples.

Test Example 1 Test for Determining Herbicidal Activity by Paddy FieldSoil Treatment

A 100 cm² wide plastic pot was filled with a paddy field soil and, afterwatering and shuffling, seeds of each of Echinochloa oryzicola,Monochoria vaginalis, and Scirpus juncoides Rocxb. were sowed andwatered to a depth of 3 cm. On the next day, the wettable powderobtained in view of Formulation example 1 was diluted with water andapplied on water surface. The application amount was 1000 g of effectivecomponent per hectare. After that, the plants were cultivated in agreenhouse, and on day 21 after the treatment, evaluation was made bythe criteria of Table 72 for determining the herbicidal effects. Theresults are shown in Table 73 to Table 76.

TABLE 72 Index Number Herbicidal Effects 10 100% of herbicidal effects(complete death) 9 90% or more and less than 100% of herbicidal effects8 80% or more and less than 90% of herbicidal effects 7 70% or more andless than 80% of herbicidal effects 6 60% or more and less than 70% ofherbicidal effects 5 50% or more and less than 60% of herbicidal effects4 40% or more and less than 50% of herbicidal effects 3 30% or more andless than 40% of herbicidal effects 2 20% or more and less than 30% ofherbicidal effects 1 10% or more and less than 20% of herbicidal effects0 0% or more and less than 10% of herbicidal effects

TABLE 73 Compound Echinochloa No. oryzicola I-1 10 I-2 10 I-3 10 I-4 9I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 9 I-19 10 I-27 10 I-41 8 I-4310 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-5810 I-59 10 I-60 10 I-61 8 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-6810 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-7910 I-80 10 I-81 10 I-82 8 I-83 10 I-84 10 I-85 10 I-86 10 I-87 9 I-88 10I-89 10 I-90 9 I-91 10 I-92 10 I-93 8 I-96 8 I-99 10 I-105 10 I-106 10I-107 10 I-108 10 I-109 10 I-110 10 I-111 10 I-115 10 I-116 10 I-117 10I-118 10 I-119 9 I-120 8 I-125 10 I-126 10 I-127 10 I-128 8 I-129 10I-131 9 I-134 10 I-135 10 I-136 9 I-137 10 I-138 10 I-149 9 I-155 10I-169 10 I-170 10 I-179 10 I-184 10 I-185 8 I-187 10 I-198 8 I-199 9I-202 10 I-203 10 I-205 7 I-259 10 I-260 10 I-261 8 I-263 10 I-265 10I-268 10 I-269 8 I-270 8 I-271 8 I-272 7 I-273 9 I-274 8 I-275 9 I-276 8I-277 9 I-278 8 I-279 8 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10I-285 10 I-286 10 I-287 10 I-288 10 I-289 10 I-292 10 I-294 9 I-297 10I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10 I-307 8I-328 10 I-339 10 I-463 10 I-464 10 I-465 10 I-466 8 I-468 10 I-469 10I-470 10 I-471 10 I-473 8 I-474 10 I-475 10 I-476 10 I-477 10 I-478 10I-479 10 I-480 10 III-50 10 III-62 8 VI-1 10 VI-5 10 VI-6 10 VI-7 10VI-65 10 VI-97 10 V-300 10 V-358 10 V-359 8 V-362 10 V-363 10 V-364 10V-365 10 V-367 8 V-368 10 V-369 10 V-370 10 V-371 10

TABLE 74 Monochoria Compound No. vaginalis I-1 10 I-2 10 I-3 10 I-4 9I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 9 I-19 10 I-27 10 I-41 8 I-4310 I-47 10 I-50 10 I-51 10 I-52 10 I-53 7 I-54 10 I-55 10 I-56 10 I-5710 I-58 10 I-59 10 I-60 10 I-61 10 I-62 8 I-63 10 I-64 10 I-65 10 I-6610 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-7710 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-8610 I-87 10 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-9610 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-11110 I-115 10 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-12610 I-127 10 I-128 9 I-129 10 I-131 10 I-134 10 I-135 10 I-136 10 I-13710 I-138 10 I-149 10 I-155 10 I-169 10 I-170 10 I-179 10 I-182 8 I-18310 I-184 10 I-185 9 I-187 10 I-189 10 I-198 10 I-199 8 I-202 10 I-203 10I-204 8 I-205 10 I-259 10 I-260 10 I-261 10 I-262 8 I-263 10 I-265 10I-268 10 I-269 8 I-270 8 I-271 8 I-272 8 I-273 9 I-274 8 I-275 10 I-2768 I-277 9 I-278 9 I-279 8 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10I-285 10 I-286 10 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10 I-292 10I-293 10 I-294 9 I-297 10

TABLE 75 Monochoria Compound No. vaginalis I-298 10 I-299 10 I-300 10I-301 10 I-302 10 I-303 10 I-304 10 I-306 9 I-307 9 I-308 8 I-328 10I-339 10 I-462 10 I-463 10 I-464 10 I-465 10 I-466 10 I-467 10 I-468 10I-469 10 I-470 10 I-471 10 I-472 10 I-473 10 I-474 10 I-475 10 I-476 10I-477 10 I-478 10 I-479 10 II-50 8 II-267 8 III-50 10 III-62 10 VI-1 10VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-291 8 V-300 10 V-358 10V-359 10 V-360 10 V-361 10 V-362 10 V-363 10 V-364 10 V-365 10 V-366 10V-367 10 V-368 10 V-369 10 V-370 10 V-371 10

TABLE 76 Compound S. juncoides No. Rocxb. I-1 10 I-2 10 I-3 10 I-4 10I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 10 I-19 10 I-27 10 I-41 10I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-63 10 I-64 10 I-65 10 I-66 10I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10I-87 10 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10I-115 10 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10I-127 10 I-128 10 I-129 10 I-131 10 I-134 10 I-135 10 I-136 10 I-137 10I-138 10 I-149 10 I-155 10 I-169 10 I-170 10 I-179 10 I-182 9 I-183 10I-184 10 I-185 9 I-187 10 I-189 10 I-198 10 I-199 9 I-202 10 I-203 10I-205 10 I-259 10 I-260 10 I-261 8 I-263 10 I-265 10 I-268 10 I-269 10I-270 8 I-271 10 I-272 8 I-273 10 I-274 4 I-275 8 I-276 9 I-277 10 I-27810 I-279 10 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-2869 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10 I-292 10 I-293 10 I-294 9I-297 10 I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10I-307 8 I-328 10 I-339 10 I-462 10 I-463 10 I-464 10 I-465 10 I-466 10I-467 10 I-468 10 I-469 10 I-470 10 I-471 10 I-472 8 I-473 8 I-474 10I-475 10 I-476 10 I-477 10 I-478 9 I-479 10 I-480 10 II-50 7 III-50 10III-62 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 10V-358 10 V-359 10 V-360 10 V-361 10 V-362 10 V-363 10 V-364 10 V-365 10V-366 8 V-367 8 V-368 10 V-369 10 V-370 10 V-371 9

Test Example 2 Test for Determining Herbicidal Activity by Field SoilTreatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of eachof Echinochloa crus-galli, foxtail. Indian millet, and A. retroflexuswere sowed and then covered with soil. The wettable powder produced withreference to the Formulation example 1 was diluted water, and applied onthe soil surface by using a small sprayer in an amount of 1000 litersper hectare so that the effective component is 1000 g per hectare. Afterthat, the plants were cultivated in a greenhouse, and on day 21 afterthe treatment, evaluation was made by the criteria described in Table 72for determining the herbicidal effects. The results are shown in Table77 to Table 80.

TABLE 77 Echinochloa Compound No. crus-galli I-1 8 I-2 10 I-3 10 I-4 9I-5 10 I-9 7 I-10 10 I-11 10 I-14 10 I-16 9 I-19 8 I-27 10 I-41 9 I-4310 I-50 10 I-51 10 I-52 10 I-53 8 I-54 10 I-55 10 I-56 10 I-57 10 I-5810 I-60 10 I-61 8 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-7110 I-72 9 I-73 9 I-74 10 I-75 9 I-76 10 I-77 9 I-78 10 I-79 9 I-80 9I-81 9 I-82 9 I-83 9 I-84 9 I-85 9 I-86 10 I-87 9 I-88 8 I-89 9 I-90 8I-91 9 I-92 9 I-93 7 I-98 7 I-99 8 I-105 9 I-106 10 I-107 8 I-109 9I-110 7 I-111 9 I-115 9 I-116 10 I-117 10 I-118 10 I-119 8 I-120 8 I-1257 I-127 10 I-128 8 I-129 9 I-131 9 I-134 10 I-135 9 I-137 10 I-138 9I-149 8 I-167 8 I-169 10 I-179 10 I-182 7 I-184 8 I-185 9 I-187 7 I-1987 I-199 9 I-202 10 I-203 9 I-259 10 I-260 10 I-265 10 I-269 8 I-270 8I-271 10 I-273 9 I-274 7 I-275 8 I-276 9 I-277 8 I-278 9 I-279 7 I-280 9I-281 9 I-282 10 I-283 9 I-284 10 I-285 10 I-286 10 I-287 10 I-288 10I-289 9 I-292 7 I-294 9 I-297 10 I-298 7 I-299 9 I-302 7 I-303 9 I-30410 I-307 7 I-339 8 I-471 7 I-474 7 I-475 7 I-476 7 I-477 9 I-478 9 I-4799 I-480 8 VI-5 8 VI-7 10 V-300 7 V-365 7 V-368 7 V-369 7 V-370 7 V-371 9

TABLE 78 Setaria Compound No. viridis I-1 7 I-2 7 I-3 10 I-4 9 I-5 7I-10 10 I-11 7 I-14 10 I-16 9 I-19 8 I-41 7 I-50 10 I-51 10 I-52 10 I-5410 I-55 10 I-56 10 I-57 10 I-58 8 I-63 10 I-66 10 I-67 10 I-68 10 I-71 6I-72 10 I-73 8 I-74 7 I-75 7 I-76 9 I-77 9 I-79 10 I-80 9 I-81 7 I-82 9I-83 9 I-84 9 I-85 9 I-86 9 I-87 6 I-89 8 I-91 10 I-92 9 I-93 6 I-98 7I-99 6 I-105 7 I-109 6 I-111 7 I-116 9 I-117 7 I-118 9 I-127 8 I-128 9I-129 10 I-131 7 I-134 10 I-136 8 I-137 9 I-155 7 I-169 10 I-179 10I-202 9 I-260 5 I-265 10 I-269 9 I-270 7 I-271 10 I-276 9 I-277 8 I-2789 I-280 8 I-281 9 I-282 10 I-283 8 I-284 8 I-285 10 I-286 9 I-288 9I-289 7 I-294 7 I-297 9 I-298 7 I-299 10 I-303 9 I-304 9 VI-7 10 VI-65 7

TABLE 79 Compound Abutilon No. theophrasti I-1 9 I-2 10 I-3 10 I-4 9 I-510 I-10 10 I-11 9 I-14 10 I-16 9 I-27 10 I-41 8 I-50 10 I-51 10 I-52 10I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 9 I-81 10 I-82 9I-83 10 I-84 10 I-85 10 I-86 9 I-87 9 I-88 10 I-89 10 I-90 10 I-91 10I-92 10 I-93 10 I-94 10 I-96 10 I-98 7 I-99 9 I-105 9 I-106 10 I-107 10I-108 8 I-109 10 I-110 10 I-111 9 I-115 9 I-116 10 I-117 10 I-118 9I-119 9 I-120 9 I-125 8 I-126 10 I-127 10 I-128 10 I-129 10 I-131 9I-134 10 I-135 9 I-136 9 I-137 10 I-138 9 I-149 10 I-155 10 I-167 10I-169 9 I-170 10 I-179 10 I-182 10 I-183 10 I-184 10 I-185 10 I-187 9I-189 10 I-198 10 I-199 10 I-202 9 I-259 8 I-260 10 I-261 10 I-263 8I-265 10 I-268 8 I-269 9 I-271 10 I-273 7 I-274 8 I-275 10 I-276 10I-277 7 I-279 10 I-280 9 I-281 9 I-282 9 I-283 9 I-284 9 I-285 10 I-2869 I-287 9 I-288 9 I-289 9 I-290 10 I-291 10 I-292 9 I-293 10 I-294 9I-297 9 I-298 10 I-299 10 I-300 10 I-302 10 I-303 9 I-304 10 I-306 7I-307 9 I-339 10 I-462 10 I-463 10 I-465 10 I-470 7 I-471 10 I-474 10I-475 7 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 VI-1 10 VI-5 10VI-6 9 VI-7 10 VI-65 10 V-61 8 V-300 9 V-358 10 V-361 10 V-364 7 V-36510 V-368 10 V-369 7 V-370 10 V-371 10

TABLE 80 Compound Amaranthus No. retroflexus I-1 10 I-2 10 I-3 10 I-4 10I-5 10 I-9 10 I-10 10 I-11 10 I-14 10 I-16 10 I-19 8 I-27 10 I-41 10I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 9I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-63 10 I-64 10 I-65 10 I-66 10I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10I-87 9 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10I-115 9 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10I-127 10 I-128 10 I-129 10 I-131 10 I-134 10 I-135 10 I-136 9 I-137 10I-138 10 I-149 10 I-155 10 I-167 10 I-169 10 I-170 10 I-179 9 I-182 10I-183 8 I-184 10 I-185 10 I-187 10 I-189 10 I-198 10 I-199 10 I-202 10I-203 7 I-259 10 I-260 10 I-263 10 I-265 10 I-268 10 I-269 10 I-270 10I-271 10 I-272 8 I-273 10 I-274 7 I-275 10 I-276 10 I-277 8 I-278 10I-279 10 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-286 10I-287 10 I-288 10 I-289 10 I-290 8 I-291 8 I-294 10 I-297 10 I-298 10I-299 10 I-300 10 I-302 10 I-303 10 I-304 10 I-306 10 I-307 10 I-308 10I-339 10 I-462 9 I-463 7 I-464 7 I-465 10 I-468 7 I-470 8 I-471 10 I-47410 I-475 7 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 VI-1 10 VI-5 10VI-6 10 VI-7 10 VI-65 10 V-300 10 V-358 10 V-361 8 V-362 7 V-364 8 V-36510 V-368 10 V-369 7 V-370 10 V-371 10

Test Example 3 Test for Determining Herbicidal Activity by Field FoliageTreatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of eachof Indian millet and A. retroflexus were sowed and then incubated for 2weeks in a green house. The wettable powder produced with reference tothe Formulation example 1 was diluted water, and applied from the air toentire body of the plant as foliage treatment by using a small sprayerin an amount of 1000 liters per hectare so that the effective componentis 1000 g per hectare. After that, the plants were cultivated in agreenhouse, and on day 14 after the treatment, evaluation was made bythe criteria described in Table 72 for determining the herbicidaleffects. The results are shown in Table 81 to Table 84.

Compound Echinochloa No. crus-galli I-1 8 I-2 9 I-3 9 I-4 9 I-5 10 I-910 I-10 8 I-11 9 I-14 9 I-16 9 I-19 10 I-27 9 I-41 10 I-43 8 I-50 10I-51 10 I-52 10 I-53 8 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 7I-60 10 I-61 9 I-63 10 I-64 10 I-65 8 I-66 10 I-67 10 I-68 10 I-71 10I-72 10 I-73 10 I-74 9 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10I-81 10 I-82 10 I-83 10 I-84 9 I-85 9 I-86 9 I-87 9 I-88 8 I-89 9 I-90 8I-91 9 I-92 10 I-93 9 I-96 7 I-98 7 I-99 9 I-105 10 I-106 10 I-107 7I-109 10 I-110 9 I-111 10 I-115 10 I-116 9 I-117 9 I-118 9 I-119 9 I-1209 I-125 10 I-126 9 I-127 10 I-128 9 I-129 10 I-131 10 I-134 10 I-135 10I-136 9 I-137 10 I-138 8 I-149 8 I-155 9 I-167 10 I-169 9 I-170 10 I-17910 I-182 8 I-184 10 I-185 10 I-187 8 I-198 10 I-199 10 I-202 9 I-203 6I-259 10 I-260 8 I-263 9 I-265 8 I-268 7 I-269 10 I-270 9 I-271 10 I-2726 I-273 10 I-274 9 I-275 9 I-276 10 I-277 10 I-278 10 I-279 9 I-280 9I-281 9 I-282 8 I-283 8 I-284 9 I-285 9 I-286 10 I-287 8 I-288 9 I-289 9I-292 8 I-294 9 I-297 9 I-298 10 I-299 8 I-300 9 I-302 10 I-303 8 I-30410 I-328 7 I-339 9 I-463 7 I-465 8 I-467 8 I-468 9 I-469 10 I-470 8I-471 9 I-474 7 I-475 9 I-476 7 I-477 9 I-478 8 I-479 9 I-480 9 III-5010 VI-1 10 VI-5 10 VI-6 8 VI-7 10 VI-65 9 VI-97 7 V-300 8 V-358 8 V-3608 V-362 9 V-363 10 V-364 8 V-365 9 V-368 7 V-369 9 V-370 7 V-371 8

TABLE 82 Setaria Compound No. viridis I-1 8 I-2 10 I-3 9 I-4 9 I-5 10I-10 7 I-11 9 I-14 10 I-16 9 I-19 10 I-27 6 I-41 10 I-43 8 I-50 10 I-5110 I-52 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-60 9 I-63 10 I-6610 I-67 10 I-68 8 I-71 9 I-72 10 I-73 10 I-74 9 I-75 10 I-76 9 I-77 10I-78 10 I-79 10 I-80 7 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 9I-89 10 I-90 7 I-91 10 I-92 10 I-93 9 I-105 7 I-109 7 I-116 9 I-117 9I-118 10 I-126 7 I-127 10 I-128 10 I-129 9 I-134 10 I-136 9 I-137 10I-138 8 I-155 7 I-167 8 I-169 9 I-179 10 I-184 8 I-185 9 I-187 8 I-199 8I-202 9 I-261 7 I-263 9 I-265 9 I-269 8 I-271 7 I-274 8 I-275 8 I-276 10I-277 9 I-278 10 I-281 7 I-282 7 I-284 7 I-285 9 I-286 10 I-288 10 I-2897 I-297 9 I-298 8 I-302 10 I-303 10 I-304 10 I-328 7 I-463 7 I-464 7I-465 10 I-468 9 I-469 10 I-470 9 I-471 10 I-475 7 I-479 7 VI-1 10 VI-510 VI-6 10 VI-7 10 VI-65 7 VI-97 10 V-300 8 V-358 10 V-362 9 V-363 10V-364 9 V-365 10 V-369 7

TABLE 83 Compound Abutilon No. theophrasti I-1 9 I-2 10 I-3 9 I-4 9 I-510 I-9 10 I-10 9 I-11 9 I-14 10 I-16 9 I-19 10 I-27 9 I-41 10 I-43 9I-47 9 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10I-58 10 I-59 10 I-60 10 I-61 10 I-62 9 I-63 10 I-64 10 I-65 10 I-66 10I-67 10 I-68 10 I-71 9 I-72 10 I-73 10 I-74 9 I-75 10 I-76 10 I-77 10I-78 10 I-79 10 I-80 9 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10I-87 9 I-88 9 I-89 10 I-90 9 I-91 10 I-92 10 I-93 10 I-94 10 I-96 9 I-989 I-99 10 I-105 10 I-106 9 I-107 9 I-108 9 I-109 9 I-110 9 I-111 10I-115 10 I-116 9 I-117 9 I-118 10 I-119 9 I-120 9 I-125 10 I-126 9 I-1279 I-128 10 I-129 9 I-131 10 I-134 10 I-135 10 I-136 9 I-137 10 I-138 9I-149 10 I-155 10 I-167 10 I-169 9 I-170 10 I-179 10 I-182 9 I-183 9I-184 9 I-185 9 I-187 9 I-189 9 I-198 10 I-199 9 I-202 9 I-203 9 I-20510 I-259 10 I-260 10 I-261 10 I-263 10 I-265 9 I-268 9 I-269 9 I-270 9I-271 9 I-272 9 I-273 9 I-274 8 I-275 9 I-276 9 I-277 9 I-278 9 I-279 10I-280 9 I-281 9 I-282 9 I-283 8 I-284 8 I-285 7 I-286 9 I-287 9 I-288 10I-289 9 I-290 9 I-291 9 I-292 10 I-293 8 I-294 7 I-295 9 I-297 8 I-298 9I-299 9 I-300 8 I-301 7 I-302 10 I-303 9 I-304 9 I-306 9 I-307 10 I-3088 I-328 10 I-339 10 I-462 10 I-463 9 I-464 10 I-465 10 I-466 10 I-467 7I-468 10 I-469 10 I-470 10 I-471 10 I-472 7 I-473 10 I-474 9 I-475 8I-476 9 I-477 9 I-478 9 I-479 9 I-480 10 II-50 8 II-267 9 III-50 10III-62 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 9V-358 10 V-359 10 V-360 7 V-361 9 V-362 10 V-363 10 V-364 10 V-365 10V-366 7 V-367 10 V-368 9 V-369 8 V-370 9 V-371 9

Compound Amaranthus No. retroflexus I-1 10 I-2 10 I-3 9 I-4 9 I-5 10 I-910 I-10 10 I-11 10 I-14 10 I-16 10 I-19 10 I-27 9 I-41 10 I-43 10 I-4710 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-5810 I-59 10 I-60 10 I-61 10 I-62 10 I-63 10 I-64 10 I-65 10 I-66 10 I-6710 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-7810 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-8710 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-988 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 9 I-110 9 I-111 10I-115 10 I-116 8 I-117 8 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10I-127 10 I-128 10 I-129 10 I-131 10 I-134 10 I-135 10 I-136 10 I-137 10I-138 10 I-149 10 I-155 10 I-167 10 I-169 8 I-170 10 I-179 10 I-182 9I-183 10 I-184 10 I-185 10 I-187 10 I-189 10 I-198 10 I-199 9 I-202 9I-203 10 I-204 7 I-205 10 I-259 10 I-260 10 I-261 10 I-263 10 I-265 10I-268 10 I-269 10 I-270 10 I-271 10 I-272 10 I-273 10 I-274 9 I-275 9I-276 10 I-277 10 I-278 10 I-279 10 I-280 10 I-281 9 I-282 8 I-283 8I-284 9 I-285 8 I-286 10 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10I-292 10 I-293 10 I-294 8 I-295 8 I-297 8 I-298 10 I-299 10 I-300 10I-301 10 I-302 10 I-303 10 I-304 10 I-306 7 I-307 9 I-328 10 I-339 10I-462 10 I-463 10 I-464 10 I-465 10 I-466 10 I-467 10 I-468 10 I-469 10I-470 10 I-471 10 I-472 10 I-473 3 I-474 9 I-475 9 I-476 10 I-477 10I-478 10 I-479 10 I-480 10 II-50 10 III-50 10 III-62 10 VI-1 10 VI-5 10VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 10 V-358 10 V-359 10 V-360 10V-361 10 V-362 10 V-363 10 V-364 10 V-365 10 V-366 10 V-368 9 V-369 9V-370 10 V-371 10

As a result of the tests, it was found that the compounds of theinvention have an excellent herbicidal activity.

The invention claimed is:
 1. A triazine derivative or a salt thereofrepresented by following Formula 1,

wherein: R¹ is selected from the group consisting of a hydrogen atom, aC₁-C₁₂ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, aC₃-C₆ cycloalkyl group, a C₃-C₆ cycloalkenyl group, a C₃-C₆ cycloalkylC₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₂-C₆ haloalkenyl group, aC₂-C₆ haloalkynyl group, a C₃-C₆ halocycloalkyl group, a C₃-C₆halocycloalkyl C₁-C₆ alkyl group, an amino C₁-C₆ alkyl group, a nitroC₁-C₆ alkyl group, a C₁-C₆ alkylamino C₁-C₆ alkyl group, a di(C₁-C₆alkyl)amino C₁-C₆ alkyl group, a C₁-C₆ alkylthio C₁-C₆ alkyl group, aC₁-C₆ alkylsulfinyl C₁-C₆ alkyl group, a C₁-C₆ alkylsulfonyl C₁-C₆ alkylgroup, a C₁-C₆ haloalkylthio C₁-C₆ alkyl group, a C₁-C₆haloalkylsulfinyl C₁-C₆ alkyl group, a C₁-C₆ haloalkylsulfonyl C₁-C₆alkyl group, a C₁-C₆ alkoxy C₁-C₆ alkyl group, a hydroxy C₁-C₆ alkylgroup, a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group wherein said phenyl inthe group may be substituted with one substituent group selected fromsubstituent group α or 2 to 5 substituent groups that are the same ordifferent from each other and selected from substituent group α, a C₁-C₆alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group, a C₃-C₆ cycloalkyloxy C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group, a phenyloxyC₁-C₆ alkyl group wherein said phenyl in the group may be substitutedwith 1 to 5 identical or different substituents selected fromsubstituent group α, a phenylthio C₁-C₆ alkyl group wherein said phenylin the group may be substituted with 1 to 5 identical or differentsubstituents selected from substituent group α, a phenylsulfinyl C₁-C₆alkyl group wherein said phenyl in the group may be substituted with 1to 5 identical or different substituents selected from substituent groupα, a phenylsulfonyl C₁-C₆ alkyl group wherein said phenyl in the groupmay be substituted with 1 to 5 identical or different substituentsselected from substituent group α, a C₁-C₆ haloalkoxy C₁-C₆ alkyl group,a phenyl group which may be substituted with one or more substituentsselected from substituent group α, a phenyl C₁-C₆ alkyl group which maybe substituted with one or more substituents selected from substituentgroup α, a phenyl C₂-C₆ alkenyl group which may be substituted with oneor more substituents selected from substituent group α, a phenyl C₂-C₆alkynyl group which may be substituted with one or more substituentsselected from substituent group α, a C₁-C₆ alkoxyimino C₁-C₆ alkylgroup, a phenoxyimino C₁-C₆ alkyl group which may be substituted withone or more substituents selected from substituent group α, a di(C₁-C₆alkoxy)C₁-C₆ alkyl group, a (R³¹R³²N—C═O)C₁-C₆ alkyl group, a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group, a C₁-C₆ alkylcarbonyl C₁-C₆ alkylgroup, a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, a C₁-C₆ alkylideneaminooxy C₁-C₆ alkyl group, a formyl C₁-C₆ alkyl group, a C₁-C₆alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group, a C₁-C₆ alkylsulfinyl C₁-C₆alkoxy C₁-C₆ alkyl group, a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkylgroup, a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group, a cyano C₁-C₆ alkylgroup, a C₂-C₆ alkylidene amino group, a di(C₁-C₁₀ alkyl)amino C₁-C₆alkylidene amino group, a NR³¹R³² group, a C₁-C₆ alkoxy group, a C₂-C₆alkenyloxy group, a C₂-C₆ alkynyloxy group, a C₃-C₆ cycloalkyloxy group,a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ haloalkoxy group, aC₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to10 carbon atoms and one or more identical or different heteroatomsselected from the group consisting of an oxygen atom, a sulfur atom, anda nitrogen atom wherein the heterocyclic group may be substituted with 1to 5 identical or different substituents selected from substituent groupα, a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclicgroup comprising 3 to 10 carbon atoms and one or more identical ordifferent heteroatoms selected from the group consisting of an oxygenatom, a sulfur atom, and a nitrogen atom wherein the heterocyclic groupmay be substituted with 1 to 5 identical or different substituentsselected from substituent group α, a C₁-C₆ alkoxy C₁-C₆ alkyl groupsubstituted with a heterocyclic-oxy group in which the heterocyclicgroup in the heterocyclic-oxy group comprising 3 to 10 carbon atoms andone or more identical or different heteroatoms selected from the groupconsisting of an oxygen atom, a sulfur atom, and a nitrogen atom whereinsaid heterocyclic group optionally substituted with 1 to 5 identical ordifferent substituents selected from substituent group α, and aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from the group consisting ofan oxygen atom, a sulfur atom, and a nitrogen atom wherein theheterocyclic group may be substituted with 1 to 5 identical or differentsubstituents selected from substituent group α, and when the heteroatomin the heterocyclic group is a sulfur atom, the sulfur atom beingoptionally oxidized to sulfoxide or sulfone; R² is selected from thegroup consisting of, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆alkynyl group, a C₃-C₆ cycloalkyl group, a C₁-C₆ haloalkyl group, aC₂-C₆ haloalkenyl group, a C₂-C₆ haloalkynyl group, a C₁-C₆ alkoxy C₁-C₆alkyl group, a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group, a di(C₁-C₆ alkoxy)C₁-C₆ alkyl group, a heterocyclic group comprising 3 to 10 carbon atomsand one or more identical or different heteroatoms selected from thegroup consisting of an oxygen atom, a sulfur atom, and a nitrogen atomwherein the heterocyclic group may be substituted with 1 to 5 identicalor different substituents selected from substituent group α; a phenylgroup which may be substituted with one or more substituents selectedfrom substituent group α, a phenyl C₁-C₆ alkyl group which may besubstituted with one or more substituents selected from substituentgroup α, a phenyl C₂-C₆ alkenyl group which may be substituted with oneor more substituents selected from substituent group α, and a phenylC₂-C₆ alkynyl group which may be substituted with one or moresubstituents selected from substituent group α; Y and Z are selectedfrom the group consisting of an oxygen atom and a sulfur atom; A isselected from the group consisting of A-1, A-2, A-3, A-4, and A-5, asdepicted below;

R⁴ is selected from the group consisting of a hydroxyl group, O⁻M⁺wherein M⁺ represents an alkali metal cation or an ammonium cation, anamino group, a halogen atom, a cyano group, an isothiocyanate group, anisocyanate group, a hydroxycarbonyloxy group, a C₁-C₆ alkoxycarbonyloxygroup, a benzyloxycarbonyloxy group which may be substituted with asubstituent group selected from substituent group α, a C₁-C₆ alkoxygroup, a C₂-C₆ alkenyloxy group, a C₂-C₆ alkynyloxy group, a C₃-C₆cycloalkyloxy group, a cyanomethylene oxy group, a C₃-C₆ cycloalkylC₁-C₆ alkyloxy group, a C₁-C₆ alkylcarbonyloxy group, a C₁-C₆haloalkylcarbonyloxy group, a C₂-C₆ alkenylcarbonyloxy group, a C₂-C₆haloalkenylcarbonyloxy group, a C₂-C₆ alkynylcarbonyloxy group, a C₂-C₆haloalkynylcarbonyloxy group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group,a phenyloxy group which may be substituted with one or more substituentsselected from substituent group α, a benzyloxy group which may besubstituted with one or more substituents selected from the substituentgroup α, a phenylcarbonyloxy group which may be substituted with one ormore substituents selected from substituent group α, a benzylcarbonyloxygroup which may be substituted with one or more substituents selectedfrom substituent group α, a phenylcarbonyl C₁-C₆ alkyloxy group whichmay be substituted with one or more substituents selected fromsubstituent group α, a C₁-C₁₀ alkylsulfonlyoxy group, a C₁-C₆haloalkylsulfonlyoxy group, a phenylsulfonyloxy group which may besubstituted with one or more substituents selected from substituentgroup α, a benzylsulfonyloxy group which may be substituted with one ormore substituents selected from substituent group α, a C₁-C₁₀ alkylthiogroup, a C₁-C₁₀ alkylsulfinyl group, a C₁-C₁₀ alkylsulfonyl group, aC₁-C₆ haloalkylthio group, a C₁-C₆ haloalkylsulfinyl group, a C₁-C₆haloalkylsulfonyl group, a C₂-C₆ alkenylthio group, a C₂-C₆alkenylsulfinyl group, a C₂-C₆ alkenylsulfonyl group, a C₂-C₆alkynylthio group, a C₂-C₆ alkynylsulfinyl group, a C₂-C₆alkynylsulfonyl group, a phenylthio group which may be substituted withone or more substituents selected from substituent group α, a benzylthiogroup which may be substituted with one or more substituents selectedfrom substituent group α, a phenylsulfinyl group which may besubstituted with one or more substituents selected from substituentgroup α, a benzylsulfinyl group which may be substituted with one ormore substituents selected from substituent group α, a phenylsulfonylgroup which may be substituted with one or more substituents selectedfrom substituent group α, a benzylsulfonyl group which may besubstituted with one or more substituents selected from substituentgroup α, a C₁-C₁₀ alkylamino group, a di(C₁-C₁₀ alkyl)amino group, aC₁-C₆ alkoxycarbonylamino group, a C₁-C₆ alkoxy group substituted with aheterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from the group consisting ofan oxygen atom, a sulfur atom, and a nitrogen atom wherein theheterocyclic group may be substituted with 1 to 5 identical or differentsubstituents selected from substituent group α, a heterocyclic groupcomprising 3 to 10 carbon atoms and one or more identical or differentheteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogenatom wherein the heterocyclic group may be substituted with 1 to 5identical or different substituents selected from substituent group α,and a heterocyclic-oxy group in which the heterocyclic group in theheterocyclic-oxy group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from the group consisting ofan oxygen atom, a sulfur atom, and a nitrogen atom wherein theheterocyclic group may be substituted with 1 to 5 identical or differentsubstituents selected from substituent group α; A₁ is selected from thegroup consisting of X₁ and X₂, as depicted by the following formulas

A₂ is selected from the group consisting of X₃, X₄, X₅, X₆, and X₇, asdepicted by the following formulas

A₃ is selected from the group consisting of X₈ and X₉, as depicted bythe following formulas

n is selected from the group consisting of 0, 1, and 2; R⁵, R⁶, R⁸, R⁹,R³⁵ and R³⁶ are each independently selected from the group consisting ofa hydrogen atom and a C₁-C₆ alkyl group, wherein, R⁵ and R⁸ may bejoined together to form a C₂-C₅ alkylene chain or a C₂-C₅ alkenylenechain, and may form a ring together with adjacent carbon atoms, and R⁵and R³⁵ may be joined together to form a C₁-C₅ alkylene chain to form aring with adjacent carbon atoms; R⁷, R³³, and R³⁴ are each independentlyselected from the group consisting of a hydrogen atom, a C₁-C₆ alkylgroup, a C₁-C₆ haloalkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynylgroup, and a C₁-C₆ alkoxy group; R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are eachindependently selected from the group consisting of a hydrogen atom, aC₁-C₆ alkyl group, a C₁-C₆ alkoxy group, and a benzyl group which may besubstituted with one or more substituents selected from the substituentgroup α; R¹⁸ is selected from the group consisting of a hydrogen atom, aC₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, acyanomethyl group, and a benzyl group; R²⁰ is selected from the groupconsisting of a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆alkynyl group, a C₃-C₆ cycloalkyl group, and a C₃-C₆ cycloalkyl C₁-C₆alkyl group; R²¹ is selected from the group consisting of a hydrogenatom; a C₁-C₆ alkyl group, and a halogen atom; R²³ is selected from thegroup consisting of a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, aC₃-C₆ cycloalkyl group, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinylgroup, a C₁-C₁₀ alkylsulfonyl group, a phenylthio group which may besubstituted with one or more substituents selected from the substituentgroup α, a benzylthio group which may be substituted with one or moresubstituents selected from substituent group α, a phenylsulfinyl groupwhich may be substituted with one or more substituents selected fromsubstituent group α, a benzylsulfinyl group which may be substitutedwith one or more substituents selected from substituent group α, aphenylsulfonyl group which may be substituted with one or moresubstituents selected from substituent group α, and a benzylsulfonylgroup which may be substituted with one or more substituents selectedfrom substituent group α; R²⁴ is selected from the group consisting of ahydrogen atom, a halogen atom, a cyano group, a C₁-C₆ alkyl group, aC₃-C₆ cycloalkyl group, and a C₁-C₆ alkoxycarbonylamino group; R²⁵ isselected from the group consisting of a C₁-C₆ alkoxycarbonyl group, acyano group, and a nitro group; R³¹ and R³² are each independentlyselected from the group consisting of a hydrogen atom, a C₁-C₆ alkylgroup, a phenyl group which may be substituted with one or moresubstituents selected from substituent group α, a benzyl group which maybe substituted with one or more substituents selected from thesubstituent group α, a C₁-C₆ alkoxy C₁-C₆ alkyl group, a C₁-C₆alkylcarbonyl group, a C₁-C₁₀ alkylthio carbonyl group, a C₁-C₆alkoxycarbonyl group, a C₁-C₆ haloalkyl group, a C₃-C₆ cycloalkyl group,a C₃-C₆ cycloalkyl C₁-C₆ alkyl group, a C₁-C₆ alkylsulfonyl group, aphenylsulfonyl group which may be substituted with one or moresubstituents selected from substituent group α, a benzylsulfonyl groupwhich may be substituted with one or more substituents selected fromsubstituent group α, a heterocyclic group comprising 3 to 10 carbonatoms and one or more identical or different heteroatoms selected fromthe group consisting of an oxygen atom, a sulfur atom, and a nitrogenatom wherein said heterocyclic group may be substituted with 1 to 5identical or different substituents selected from substituent group α,and a C₁-C₆ alkyl group substituted with a heterocyclic group in whichthe heterocyclic group comprising 3 to 10 carbon atoms and one or moreidentical or different heteroatoms selected from an oxygen atom, asulfur atom, and a nitrogen atom wherein said heterocyclic group may besubstituted with 1 to 5 identical or different substituents selectedfrom substituent group α, wherein R³¹ and R³² may be joined together toform a 5- to 6-membered ring with adjacent nitrogen atom, and one ormore carbon atoms in the ring may be substituted with a sulfur atomand/or an oxygen atom; wherein, “substituent group α” is selected fromthe group consisting of: a halogen atom, a hydroxyl group, a C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl group, a C₃-C₆ cycloalkyl C₁-C₆ alkyl group, aC₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a C₁-C₆ haloalkyl group, aC₂-C₆ haloalkenyl group, a C₂-C₆ haloalkynyl group, a C₃-C₆halocycloalkyl group, a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a C₃-C₆ cycloalkyloxy group, a C₂-C₆ alkenyloxy group, aC₂-C₆ alkynyloxy group, a C₁-C₆ alkylcarbonyloxy group, a C₁-C₆haloalkoxy group, a C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group,a C₁-C₆ alkylsulfonyl group, a C₁-C₆ haloalkylthio group, a C₁-C₆haloalkylsulfinyl group, a C₁-C₆ haloalkylsulfonyl group, an aminogroup, a C₁-C₆ alkylcarbonylamino group, a mono(C₁-C₆ alkyl)amino group,a di(C₁-C₆ alkyl)amino group, a hydroxy C₁-C₆ alkyl group, a C₁-C₆alkoxy C₁-C₆ alkyl group, a C₁-C₆ alkylthio C₁-C₆ alkyl group, a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, a C₁-C₆ alkylsulfonyl C₁-C₆ alkylgroup, a C₁-C₆ haloalkylthio C₁-C₆ alkyl group, a C₁-C₆haloalkylsulfinyl C₁-C₆ alkyl group, a C₁-C₆ haloalkylsulfonyl C₁-C₆alkyl group, a cyano C₁-C₆ alkyl group, a C₁-C₆ alkoxy C₁-C₆ alkoxygroup, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ haloalkoxy C₁-C₆alkoxy group, a cyano C₁-C₆ alkoxy group, a C₁-C₆ acyl group, a C₁-C₆alkoxyimino C₁-C₆ alkyl group, a carboxyl group, a C₁-C₆ alkoxycarbonylgroup, a carbamoyl group, a mono(C₁-C₆ alkyl)aminocarbonyl group, adi(C₁-C₆ alkyl)aminocarbonyl group, a nitro group, a cyano group, aphenyl group optionally substituted with 1 to 5 identical or differentsubstituents selected from substituent group β, a heterocyclic groupcomprising 2 to 10 carbon atoms and 1 to 5 identical or differentheteroatoms selected from the group consisting of an oxygen atom, asulfur atom, and a nitrogen atom wherein said heterocyclic group may besubstituted with 1 to 5 identical or different substituents selectedfrom substituent group β, a heterocyclic oxy group comprising 2 to 10carbon atoms and 1 to 5 identical or different heteroatoms selected fromthe group consisting of an oxygen atom, a sulfur atom, and a nitrogenatom wherein said heterocyclic oxy group may be substituted with 1 to 5identical or different substituents selected from group β, and a C₃-C₆alkylene group formed with two adjacent substituent groups, wherein 1 to3 carbon atoms in the alkylene group may be substituted with an atomselected from the group consisting of an oxygen atom, a sulfur atom, anitrogen atom, and a carbon atom constituting an carbonyl group; and“substituent group β” is selected from the group consisting of a halogenatom, a nitro group, a cyano group, a C₁-C₆ alkyl group, a C₁-C₆haloalkyl group, a C₁-C₆ alkoxy group, and a C₁-C₆ haloalkoxy group. 2.The triazine derivative or a salt thereof according to claim 1, whereinA is A-1 or A-3.
 3. The triazine derivative or a salt thereof accordingto claim 1, wherein A is A-1.
 4. The triazine derivative or a saltthereof according to claim 3, wherein R⁴ represents a hydroxyl group; A₁represents a group represented by the following formula

A₂ represents a group represented by the following formula

A₃ represents a group represented by the following formula

and R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogenatom or a C₁-C₆ alkyl group.
 5. The triazine derivative or a saltthereof according to claim 4, wherein R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ eachindependently represent a hydrogen atom; R² represents a C₁-C₆ alkylgroup; and R¹ represents a phenyl group substituted with a halogen. 6.The triazine derivative or a salt thereof according to claim 1, whereinA is A-3.
 7. A triazine derivative or a salt thereof having a formula:

wherein: R¹ and R² are independently selected from C₁-C₆ alkyl, orphenyl substituted with 1 to 5 identical or different substituentsselected from the substituent group α, wherein substituent group α is ahalogen atom; R⁴ is hydroxyl; and Y and Z are both oxygen.
 8. Thetriazine derivative or a salt thereof according to claim 7, wherein: R¹is a phenyl substituted with 1 to 5 halogen atoms selected from chloroor fluoro; and R² is methyl, ethyl or propyl.
 9. The triazine derivativeor a salt thereof according to claim 7, wherein R¹ is phenyl,substituted at any of carbons 2, 3 or 4 of the phenyl ring with chloroor fluoro and R² is methyl.
 10. The triazine derivative or a saltthereof according to claim 7, wherein R¹ is phenyl substituted with2-chloro and R² is methyl.
 11. The triazine derivative or a salt thereofaccording to claim 7, wherein R¹ is phenyl substituted with 3-chloro andR² is methyl.
 12. The triazine derivative or a salt thereof according toclaim 7, wherein R¹ is phenyl substituted with 4-chloro and R2 ismethyl.
 13. The triazine derivative or a salt thereof according to claim7, wherein R¹ is phenyl substituted with 2-fluoro and R² is methyl. 14.The triazine derivative or a salt thereof according to claim 7, whereinR¹ is phenyl substituted with 3-fluoro and R¹ is methyl.
 15. Thetriazine derivative or a salt thereof according to claim 7, wherein R¹is phenyl substituted with 4-fluoro and R² is methyl.
 16. Anagrochemical composition comprising the triazine derivative or a saltthereof according to claim 1 or claim
 7. 17. An agrochemical compositioncomprising at least one triazine derivative or a salt thereof accordingto claim 1 or claim 7, and one additional agrochemically activecomponent selected from the group consisting of a plant disease controlcomponent, a pesticidal component, an acaricidal component, annematocidal component, a synergistic agent component, an attractingcomponent, a repellent component, a herbicidal component, a safenercomponent, a microbial pesticidal component, a plant growth controlcomponent, a fertilizer component, and a soil improving agent.
 18. Theagrochemical composition of claim 17, wherein said triazine derivativeor a salt thereof and said additional agrochemically active componentare in a weight ratio of 100:1 to 1:100.
 19. The agrochemicalcomposition of claim 17, wherein said additional agrochemically activecomponent is a herbicide selected from the group consisting offluroxypyr, tembotrione, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, diclofop-P-methyl, fenoxaprop-P-ethyl, fluazifop-butyl,fluazifop-P-butyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, metamifop,propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl,quizalofop-P-tefuryl, fenthiaprop-ethyl, alloxydim, butroxydim,clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim,tralkoxydim, aminopyralid, pinoxaden, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium,pyrimisulfan, flucarbazone-sodium, thiencarbazone,propoxycarbazone-sodium, procarbazone-sodium, amidosulfuron,azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron,flazasulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron,halosulfuron-methyl, imazosulfuron, iodosulfulon-methyl-sodium,mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron,primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron,sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron,tribenuron-methyl, trifloxysulfuron-sodium, triflusulfuron-methyl,tritosulfuron, orthosulfamuron, propyrisulfuron, metazosulfuron,flucetosulfuron, cloransulam-methyl, diclosulam, florasulam,flumetsulam, metosulam, penoxsulam, pyroxsulam, HNPC-C-9908,desmedipham, phenmedipham, chloridazon, brompyrazon, ametryn, atrazine,cyanazine, desmetryne, dimethametryn, eglinazine-ethyl, prometon,prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine,terbutryn, trietazine, metamitron, metribuzin, amicarbazone, bromacil,lenacil, terbacil, pentanochlor, propanil, chlorbromuron, chlorotoluron,chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron,isoproturon, isouron, linuron, methabenzthiazuron, metobromuron,metoxuron, monolinuron, neburon, siduron, tebuthiuron, metobenzuron,bentazone, bromofenoxim, bromoxynil, ioxynil, pyridafol, pyridate,diquat, paraquat dichloride, acifluorfen-sodium, bifenox,chlomethoxyfen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fomesafen,lactofen, oxyfluorfen, cinidon-ethyl, flumiclorac-pentyl, flumioxazin,chlorphthalim, oxadiargyl, oxadiazon, pentoxazone, fluazolate,pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil,fluthiacet-methyl, thidiazimin, azafenidin, carfentrazone-ethyl,sulfentrazone, bencarbazone, flufenpyr-ethyl, profluazol, pyraclonil,SYP-298, SYP-300, norflurazon, diflufenican, picolinafen, beflubutamid,fluridone, fluorochloridone, flurtamone, mesotrione, pyrasulfotole,isoxaflutole, isoxachlortole, benzofenap, pyrazolynate, pyrazoxyfen,sulcotrione, tefuryltrion, ternbotrione, pyrasulfotole, topramezone,bicyclopyrone, 4-chloro-5-(1,3-dioxocyclohexa-2-yl)carbonyl-2,3-dihydrobenzothiophene-1,1-dioxide, aclonifen, clomazone,amitrole, glyphosate, bilanafos, glufosinate, asulam, propyzamide,tebutam, chlorthal-dimethyl, benfluralin, butralin, dinitramine,ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine,trifluralin, amiprofos-methyl, butamifos, dithiopyr, thiazopyr,carbetamide, chlorpropham, propham, swep, karbutilate, diphenamid,napropamide, naproanilide, acetochlor, alachlor, butachlor, butenachlor,diethatyl-ethyl, dimethachlor, dimethenamid, dimethenamid-P,metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor,propisochlor, S-metolachlor, thenylchlor, flufenacet, mefenacet,fentrazamide, anilofos, bromobutide, cafenstrole, indanofan, piperophos,fenoxasulfone, pyroxasulfone, ipfencarbazone, isoxaben, dichlobenil,chlorthiamid, flupoxame, dinoterb, DNOC, benfuresate, ethofumesate,dalapon, flupropanate, TCA, bensulide, butylate, cycloate, dimepiperate,EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb,thiobencarb, tiocarbazil, tri-allate, vernolate, chloramben, 2,3,6-TBA,dicamba, 2,4,5-T, 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P,MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, clopyralid,fluoroxypyr, picloram, triclopyr, triclopyr-butotyl, quinclorac,quinmerac, benazolin, naptalam, diflufenzopyr, Flamprop-M, flamprop,chlorflurenol-methyl, cinmethylin, cumyluron, daimuron, methyldymuron,difenzoquat, etobenzanid, fosamine, pyributicarb, oxaziclomefone,acrolein, AE-F-150944, aminocyclopyrachlor, cyanamide,heptamaloxyloglucan, indaziflam, triaziflam, quinoclamine,endothal-disodium, phenisopham, BDPT, BAU-9403, SYN-523, SYP-249,JS-913, IR-6396, metiozolin, Triafamone, HW-02, and BCS-AA10579.
 20. Theagrochemical composition of claim 17, wherein said additionalagrochemically active component is a plant growth controlling compoundselected from the group consisting of 1-Methylcyclopropene,1-naphthylacetamide, 2,6-diisopropylnaphthalene, 4-CPA,benzylaminopurine, ancymidol, aviglycine, carvone, chlormequat, cloprop,cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins, daminodide,dikegulac, dimethipin, ethephon, ethychlozate, flumetralin, flurenol,flurprimidol, forchlorfenuron, gibberellin acid, inabenfide, indolacetic acid, indol butyric acid, maleic hydrazide, mefluidide, mepiquatchloride, n-decanol, paclobutrazol, prohexadione-calcium,prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapac-ethyl,uniconazole, uniconazole-P, and ecolyst, benoxacor, furilazole,dichlormid, dicyclonone, DKA-24(N1,N2-diallyl-N2-dichloroacetylglycinamide), AD-67(4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane), PPG-1292(2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide),R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine),cloquintcet-mexyl, naphthalic anhydride (1,8-naphthalic anhydride),mefenpyr-diethyl, mefenpyr, mefenpyr-ethyl, fenchlorazole ethyl,fenclorim, MG-191 (2-dichloromethyl-2-methyl-1,3-dioxane), cyometrinil,flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, mecoprop, MCPA,daimuron, 2,4-D, MON4660, oxabetrinil, cyprosulfamide, lower alkylsubstituted benzoic acid, TI-35, benalaxyl, benalaxyl-M, furalaxyl,metalaxyl, metalaxyl-M, oxadixyl, clozylacon, ofurace, bupirimate,dimethirimol, ethirimol, hymexazol, octhilinone, oxolinic acid, benomyl,carbendazim, fuberidazole, thiabendazole, thiophanate,thiophanate-methyl, diethofencarb, zoxamide, pencycuron, fluopicolidediflumetorim, benodanil, flutolanil, mepronil, fluopyram, fenfuram,carboxin, oxycarboxin, thifluzamide, bixafen, furametpyr, isopyrazam,penflufen, penthiopyrad, sedaxane, boscalidazoxystrobin, enestroburin,picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin,kresoxim-methyl, trifloxystrobin, dimoxystrobin, metominostrobin,orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb,cyazofamid, amisulbrom, binapacryl, meptyldinocap, dinocap, fluazinam,ferimzone, TPTA, TPTC, TPTH, silthiofam, ametoctradin, cyprodinil,mepanipyrim, pyrimethanil, blasticidin-S, mildiomycin, kasugamycin,streptomycin, oxytetracycline, gentamycin, quinoxyfen, proquinazid,fenpiclonil, fludioxonil, chlozolinate, iprodione, rocymidone,vinclozolin, edifenphos, iprobenfos, pyrazophos, isoprothiolane,biphenyl, chloroneb, dicloran, quintozene, tecnazene, andtolclofos-methyl, etridiazole, iodocarb, propamocarb-hydrochloride,prothiocarb, dimethomorph, flumorph, benthiavalicarb-isopropyl,iprovalicarb, and valifenalate, mandipropamid, Bacillus subtilis(strain: QST 713), triforine, pyrifenox, fenarimol, nuarimol, imazalil,oxpoconazole-fumarate, pefurazoate, prochloraz, triflumizole,azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole,diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole,fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,ipconazole, metconazole, myclobutanil, penconazole, propiconazole,prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon,triadimenol, triticonazole, furconazole, furconazole-cis, quinconazole,aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin,spiroxamine, fenhexamid, pyributicarb, naftifine, terbinafinevalidamycin, polyoxin, phthalide, pyroquilon, tricyclazole, carpropamid,diclocymet, fenoxanil, acibenzolar-S-methyl, probenazole, tiadinil,isotianil, laminarin, copper hydroxide, copper dioctanoate, copperoxychloride, copper, sulfate, cuprous oxide, oxine-copper, Bordeauxmixture, and copper nonyl phenol sulphonate, sulfur, ferbam, mancozeb,maneb, metiram, propineb, thiram, zineb, ziram, cufraneb, captan,folpet, captafol, chlorothalonil, dichlofluanid, tolylfluanid,guazatine, iminoctadine-albesilate, iminoctadine-triacetate, dodine,anilazine, dithianon, cymoxanil, fosetyl-alminium, fosetyl-calcium,fosetyl-sodium, phosphorous acid and salts, tecloftalam, triazoxide,flusulfamide, diclomezine, methasulfocarb, ethaboxam, cyflufenamid,metrafenone, potassium bicarbonate, sodium bicarbonate, BAF-045,BAG-010, benthiazole, bronopol, carvone, chinomethionat, dazomet, DBEDC,debacarb, dichlorophen, difenzoquat-methyl sulfate, dimethyl disulfide,diphenylamine, ethoxyquin, flumetover, fluoroimide, flutianil,fluxapyroxad, furancarboxylic acid, metam, nabam, natamycin, nitrapyrin,nitrothal-isopropyl, o-phenylphenol, oxazinylazole, oxyquinolinesulfate, phenazine oxide, polycarbamate, pyriofenone, S-2188, silver,SYP-Z-048, tebufloquin, tolnifanide, trichlamide, mineral oils, organicoils, Agrobacterium radiobacter, Fermented product from Aspergillusspp., Bacillus spp., Harpin protein, Erwinia carotovora, Fusariumoxysporum, Gliocladium spp., Laccase, Pseudomonas spp., Talaromycesspp., Trichoderma spp., Extract from mushroom, and Bacteriophage. 21.The agrochemical composition of claim 17, wherein said additionalagrochemically active component is selected from the group consisting ofalanycarb, aldicarb, aldoxycarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, 3,5-xylyl methylcarbamate(XMC), xylylcarb,acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos,chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diamidafos,diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos,dioxabenzofos, disulfoton, DSP, EPN, ethion, ethoprophos, etrimfos,famphur, fenamiphos, fenitrothion, fenthion, fonofos, fosthiazate,fosthietan, heptenophos, isamidofos, isazophos, isofenphos-methyl,isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion,malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, oxydeprofos,parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet,phosphamidon, phoxim, pirimiphos-methyl, profenofos, propaphos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, thionazin, triazophos, trichlorfon, vamidothion,dichlofenthion, imicyafos, isocarbophos, mesulfenfos, flupyrazofos,chlordane, endosulfan, gamma-BCH, acetoprol, ethiprole, fipronil,pyrafluprole, pyriprole, RZI-02-003, acrinathrin, allethrin, bifenthrin,bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin,cycloprothrin, and cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin,deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, and tau-fluvalinate, halfenprox,imiprothrin, metofluthrin, permethrin, and phenothrin, prallethrin,profluthrin, pyrethrine, resmethrin, RU15525, silafluofen, tefluthrin,tetramethrin, tralomethrin, transfluthrin, ZXI8901, fluvalinate,tetramethylfluthrin, meperfluthrin, DDT, methoxychlor, acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid,thiamethoxam, spinetoram, spinosad, abamectin, emamectin benzoate,lepimectin, milbemectin, ivermectin, polynactins, diofenolan,hydroprene, kinoprene, methothrin, fenoxycarb, and pyriproxyfen,1,3-dichloropropene, DCIP, ethylene dibromide, methyl bromide,chloropicrin, and sulfuryl fluoride, pymetrozine, flonicamid andpyrifluquinazon, clofentezine, diflovidazin, hexythiazox, and etoxazole,diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite,tetradifon, chlorfenapyr and DNOC, bensultap, cartap, thiocyclam,thiosultap, bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron, triflumuron, fluazuron, buprofezin, cyromazine,chromafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz,cyflumetofen, hydramethylnon, acequinocyl, fluacrypyrim, andcyenopyrafen, fenazaquin, fenpyroximate, pyridaben, pyrimidifen,tebufenpyrad, tolfenpyrad, rotenone, indoxacarb and metaflumizon,spirodiclofen, spiromesifen, and spirotetramat, aluminium phosphide,phosphine, zinc phosphide, calcium cyanide, and phosphine, bifenazate,sodium fluoroacetate, chlorantraniliprole, flubendiamide andcyantraniliprole, azadirachtin, amidoflumet, benclothiaz, benzoximate,bromopropylate, chinomethionat, CL900167, cryolite, dicofol, dicyclanil,dienochlor, dinobuton, fenbutatin oxide, fenothiocarb, fluensulfone,flufenerim, flusulfamide, karanjin, metham, methoprene, methoxyfenozide,methyl isothiocyanate, pyridalyl, pyrifluquinazon, sulcofuron-sodium,sulflramid, and sulfoxaflor, piperonyl butoxide and DEF.
 22. Theagrochemical composition of claim 17, wherein said additionalagrochemically active component is selected from the group consisting of2,4-D, acetochlor, acifluorfen-na, alachlor, atrazine, bentazon,bispyribac-na, carfentrazone-ethyl, clodinafop-propargyl, clomazone,cloransulam-methyl, dicamba, di clofop-methyl, diflufenican,dimethenamid, fenoxaprop-p-ethyl, fenoxasulfone, florasulam,flucarbazone-na, flumetsulam, flumioxazin, fluroxypyr,fluthiacet-methyl, fomesafen, glufosinate, glyphosate,halosulfuron-methyl, imazamox, imazaquin, isoproturon, isoxaflutole,linuron, mesosulfuron-methyl, mesotrione, metolachlor, metribuzin,nicosulfuron, pendimethalin, pinoxaden, propoxycarbazone-na,prosulfocarb, pyriminobac-methyl, pyrithiobac-na, quinclorac,rimsulfuron, saflufenacil, sulcotrione, tembotrione,thifensulfuron-methyl, thiobencarb, topramezone, triasulfuron,trifluralin, pyroxasulfone, pethoxamid, bromoxynil, flufenacet,sulfentrazone, and S-metolachlor.
 23. The agrochemical compositioncomprising the triazine derivative or a salt thereof according to claim17, further comprising an agriculturally acceptable carrier.
 24. Theagrochemical composition according to claim 17, further comprising asurface active agent.
 25. A method of controlling the growth of weedsfor useful crops or plants, comprising applying the agrochemicalcomposition of claim
 17. 26. The method of claim 25, wherein theagrochemical composition is applied within an interval of 1 day to 40days.
 27. The method of claim 25, wherein the useful crops or plants areselected from the group consisting of rice, wheat, barley, corn, grainsorghum, soybean, cotton, and sugar beet.